U.S. patent application number 15/535526 was filed with the patent office on 2017-11-30 for organic electroluminescent device.
The applicant listed for this patent is Hodogaya Chemical Co., Ltd., SFC Co., Ltd.. Invention is credited to Soon-wook Cha, Shuichi Hayashi, Kyung-seok Jeon, Naoaki Kabasawa, Daizou Kanda, Shunji Mochizuki, Sang-woo Park, Ju-man Song, Takeshi Yamamoto, Norimasa Yokoyama.
Application Number | 20170346009 15/535526 |
Document ID | / |
Family ID | 56150312 |
Filed Date | 2017-11-30 |
United States Patent
Application |
20170346009 |
Kind Code |
A1 |
Yokoyama; Norimasa ; et
al. |
November 30, 2017 |
ORGANIC ELECTROLUMINESCENT DEVICE
Abstract
In the organic electroluminescent device having at least an
anode, a hole injection layer, a hole transport layer, a light
emitting layer, an electron transport layer and a cathode in this
order, the hole injection layer includes an arylamine compound of
the following general formula (1) and an electron acceptor.
##STR00001## In the formula, Ar.sub.4 to Ar.sub.4 may be the same
or different, and represent a substituted or unsubstituted aromatic
hydrocarbon group, a substituted or unsubstituted aromatic
heterocyclic group, or a substituted or unsubstituted condensed
polycyclic aromatic group.
Inventors: |
Yokoyama; Norimasa; (Tokyo,
JP) ; Hayashi; Shuichi; (Tokyo, JP) ;
Yamamoto; Takeshi; (Tokyo, JP) ; Kabasawa;
Naoaki; (Tokyo, JP) ; Kanda; Daizou; (Tokyo,
JP) ; Mochizuki; Shunji; (Tokyo, JP) ; Cha;
Soon-wook; (Cheongju-si, KR) ; Park; Sang-woo;
(Cheongju-si, KR) ; Song; Ju-man; (Cheongju-si,
KR) ; Jeon; Kyung-seok; (Cheongju-si, KR) |
|
Applicant: |
Name |
City |
State |
Country |
Type |
Hodogaya Chemical Co., Ltd.
SFC Co., Ltd. |
Tokyo
Cheongju-si |
|
JP
KR |
|
|
Family ID: |
56150312 |
Appl. No.: |
15/535526 |
Filed: |
December 16, 2015 |
PCT Filed: |
December 16, 2015 |
PCT NO: |
PCT/JP2015/085232 |
371 Date: |
June 13, 2017 |
Current U.S.
Class: |
1/1 |
Current CPC
Class: |
H01L 51/0061 20130101;
C07C 211/61 20130101; C09B 57/008 20130101; H01L 51/0056 20130101;
H01L 51/5072 20130101; C07D 209/86 20130101; H01L 51/5088 20130101;
C07D 209/08 20130101; H01L 51/50 20130101; C07C 211/54 20130101;
H01L 51/0067 20130101; H01L 51/0059 20130101; H01L 51/006 20130101;
C09B 1/00 20130101; H01L 51/0054 20130101; H01L 51/0072 20130101;
H01L 51/0074 20130101; C07D 333/76 20130101; C07D 235/18 20130101;
H01L 51/5012 20130101; C07C 211/58 20130101; H01L 51/5206 20130101;
C07D 239/26 20130101; H01L 51/0058 20130101; C07D 471/04 20130101;
C07D 401/10 20130101; H01L 51/5056 20130101; C07D 401/14 20130101;
C07D 307/91 20130101; C09B 57/00 20130101; H01L 51/0052 20130101;
H01L 51/5221 20130101; H01L 51/0073 20130101 |
International
Class: |
H01L 51/00 20060101
H01L051/00; C07D 401/10 20060101 C07D401/10; C07D 209/08 20060101
C07D209/08; C07D 209/86 20060101 C07D209/86; C07D 235/18 20060101
C07D235/18; C07D 239/26 20060101 C07D239/26; C07D 307/91 20060101
C07D307/91; C07D 333/76 20060101 C07D333/76; C07C 211/54 20060101
C07C211/54; C07D 471/04 20060101 C07D471/04; C07D 401/14 20060101
C07D401/14; C07C 211/61 20060101 C07C211/61; C07C 211/58 20060101
C07C211/58 |
Foreign Application Data
Date |
Code |
Application Number |
Dec 24, 2014 |
JP |
2014-259965 |
Claims
1. An organic electroluminescent device comprising at least an
anode, a hole injection layer, a hole transport layer, a light
emitting layer, an electron transport layer, and a cathode in this
order, wherein the hole injection layer comprises an arylamine
compound represented by the following general formula (1) and an
electron acceptor: ##STR00360## (wherein Ar.sub.1 to Ar.sub.4 may
be the same or different, and represent a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group).
2. The organic electroluminescent device according to claim 1,
wherein a layer adjacent to the light emitting layer does not
contain an electron acceptor.
3. The organic electroluminescent device according to claim 1,
wherein the electron acceptor is an electron acceptor selected from
trisbromophenylaminehexachloroantimony, tetracyanoquinodimethane
(TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane
(F4TCNQ), and a radialene derivative.
4. The organic electroluminescent device according to claim 1,
wherein the electron acceptor is a radialene derivative represented
by the following general formula (2): ##STR00361## (wherein
Ar.sub.5 to Ar.sub.7 may be the same or different, and represent an
aromatic hydrocarbon group, an aromatic heterocyclic group, or a
condensed polycyclic aromatic group, having an electron acceptor
group as a substituent).
5. The organic electroluminescent device according to claim 1,
wherein the hole transport layer comprises only a hole transporting
arylamine compound.
6. The organic electroluminescent device according to claim 5,
wherein the hole transport layer comprises an arylamine compound
represented by the general formula (1).
7. The organic electroluminescent device according to claim 1,
wherein the electron transport layer comprises a compound having an
anthracene ring structure represented by the following general
formula (3): ##STR00362## (wherein A.sub.1 represents a divalent
group of a substituted or unsubstituted aromatic hydrocarbon, a
divalent group of a substituted or unsubstituted aromatic
heterocyclic ring, a divalent group of a substituted or
unsubstituted condensed polycyclic aromatic, or a single bond;
B.sub.1 represents a substituted or unsubstituted aromatic
heterocyclic group; C represents a substituted or unsubstituted
aromatic hydrocarbon group, a substituted or unsubstituted aromatic
heterocyclic group, or a substituted or unsubstituted condensed
polycyclic aromatic group; D may be the same or different, and
represents a hydrogen atom, a deuterium atom, a fluorine atom, a
chlorine atom, a cyano group, a trifluoromethyl group, a linear or
branched alkyl group of 1 to 6 carbon atoms, a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group; and while p and
q maintain a relationship that the sum of p and q is 9, p
represents 7 or 8, and q represents 1 or 2).
8. The organic electroluminescent device according to claim 1,
wherein the electron transport layer comprises a compound having a
pyrimidine ring structure represented by the following general
formula (4): ##STR00363## (wherein Ar.sub.8 represents a
substituted or unsubstituted aromatic hydrocarbon group or a
substituted or unsubstituted condensed polycyclic aromatic group;
Ar.sub.9 and Ar.sub.10 may be the same or different, and represent
a hydrogen atom, a substituted or unsubstituted aromatic
hydrocarbon group, or a substituted or unsubstituted condensed
polycyclic aromatic group; and E represents a monovalent group
represented by the following structural formula (5), provided that
Ar.sub.9 and Ar.sub.10 are not simultaneously a hydrogen atom:
##STR00364## (wherein Ar.sub.11 represents a substituted or
unsubstituted aromatic heterocyclic group; R.sub.1 to R.sub.4 may
be the same or different, and represent a hydrogen atom, a
deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a
trifluoromethyl group, a linear or branched alkyl group of 1 to 6
carbon atoms, a substituted or unsubstituted aromatic hydrocarbon
group, a substituted or unsubstituted aromatic heterocyclic group,
or a substituted or unsubstituted condensed polycyclic aromatic
group).
9. The organic electroluminescent device according to claim 1,
wherein the electron transport layer comprises a compound having a
benzotriazole ring structure represented by the following general
formula (6): ##STR00365## (wherein Ar.sub.12 represents a
substituted or unsubstituted aromatic hydrocarbon group, a
substituted or unsubstituted aromatic heterocyclic group, or a
substituted or unsubstituted condensed polycyclic aromatic group;
Ar.sub.13 represents a hydrogen atom, a deuterium atom, a
substituted or unsubstituted aromatic hydrocarbon group, a
substituted or unsubstituted aromatic heterocyclic group, or a
substituted or unsubstituted condensed polycyclic aromatic group;
L.sub.1 represents a divalent group of a substituted or
unsubstituted aromatic hydrocarbon, a divalent group of a
substituted or unsubstituted aromatic heterocyclic ring, a divalent
group of a substituted or unsubstituted condensed polycyclic
aromatic, or a single bond; L.sub.2 represents a divalent group of
a substituted or unsubstituted condensed polycyclic aromatic or a
single bond; and B.sub.2 represents a substituted or unsubstituted
aromatic heterocyclic group).
10. The organic electroluminescent device according to claim 1,
wherein the light emitting layer comprises a blue light emitting
dopant.
11. The organic electroluminescent device according to claim 10,
wherein the light emitting layer comprises a blue light emitting
dopant which is a pyrene derivative.
12. The organic electroluminescent device according to claim 10,
wherein the blue light emitting dopant comprises a light emitting
dopant which is an amine derivative having a condensed ring
structure represented by the following general formula (7):
##STR00366## (wherein A.sub.2 represents a divalent group of a
substituted or unsubstituted aromatic hydrocarbon, a divalent group
of a substituted or unsubstituted aromatic heterocyclic ring, a
divalent group of a substituted or unsubstituted condensed
polycyclic aromatic, or a single bond; Ar.sub.14 and Ar.sub.15 may
be the same or different, and represent a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group, and may bind to
each other via a single bond, a substituted or unsubstituted
methylene group, an oxygen atom, or a sulfur atom to form a ring;
R.sub.5 to R.sub.8 may be the same or different, and represent a
hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom,
a cyano group, a nitro group, a linear or branched alkyl group of 1
to 6 carbon atoms that may have a substituent, a cycloalkyl group
of 5 to 10 carbon atoms that may have a substituent, a linear or
branched alkenyl group of 2 to 6 carbon atoms that may have a
substituent, a linear or branched alkyloxy group of 1 to 6 carbon
atoms that may have a substituent, a cycloalkyloxy group of 5 to 10
carbon atoms that may have a substituent, a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, a substituted or
unsubstituted condensed polycyclic aromatic group, a substituted or
unsubstituted aryloxy group, or a disubstituted amino group
substituted with a group selected from an aromatic hydrocarbon
group, an aromatic heterocyclic group, or a condensed polycyclic
aromatic group, where the respective groups may bind to each other
via a single bond, a substituted or unsubstituted methylene group,
an oxygen atom, or a sulfur atom to form a ring, or may bind to the
benzene ring to which R.sub.5 to R.sub.8 bind via a substituted or
unsubstituted methylene group, an oxygen atom, a sulfur atom, or a
monosubstituted amino group to form a ring; R.sub.9 to R.sub.11 may
be the same or different, and represent a hydrogen atom, a
deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a
nitro group, a linear or branched alkyl group of 1 to 6 carbon
atoms that may have a substituent, a cycloalkyl group of 5 to 10
carbon atoms that may have a substituent, a linear or branched
alkenyl group of 2 to 6 carbon atoms that may have a substituent, a
linear or branched alkyloxy group of 1 to 6 carbon atoms that may
have a substituent, a cycloalkyloxy group of 5 to 10 carbon atoms
that may have a substituent, a substituted or unsubstituted
aromatic hydrocarbon group, a substituted or unsubstituted aromatic
heterocyclic group, a substituted or unsubstituted condensed
polycyclic aromatic group, or a substituted or unsubstituted
aryloxy group, where the respective groups may bind to each other
via a single bond, a substituted or unsubstituted methylene group,
an oxygen atom, or a sulfur atom to form a ring, or may bind to the
benzene ring to which R.sub.9 to R.sub.11 bind via a substituted or
unsubstituted methylene group, an oxygen atom, a sulfur atom, or a
monosubstituted amino group to form a ring; and R.sub.12 and
R.sub.13 may be the same or different, and represent a linear or
branched alkyl group of 1 to 6 carbon atoms that may have a
substituent, a cycloalkyl group of 5 to 10 carbon atoms that may
have a substituent, a linear or branched alkenyl group of 2 to 6
carbon atoms that may have a substituent, a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, a substituted or
unsubstituted condensed polycyclic aromatic group, or a substituted
or unsubstituted aryloxy group, where the respective groups may
bind to each other via a single bond, a substituted or
unsubstituted methylene group, an oxygen atom, a sulfur atom, or a
monosubstituted amino group to form a ring).
13. The organic electroluminescent device according to claim 1,
wherein the light emitting layer comprises an anthracene
derivative.
14. The organic electroluminescent device according to claim 13,
wherein the light emitting layer comprises a host material which is
an anthracene derivative.
15. The organic electroluminescent device according to claim 2,
wherein the electron acceptor is an electron acceptor selected from
trisbromophenylaminehexachloroantimony, tetracyanoquinodimethane
(TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane
(F4TCNQ), and a radialene derivative.
16. The organic electroluminescent device according to claim 2,
wherein the electron acceptor is a radialene derivative represented
by the following general formula (2): ##STR00367## (wherein
Ar.sub.5 to Ar.sub.7 may be the same or different, and represent an
aromatic hydrocarbon group, an aromatic heterocyclic group, or a
condensed polycyclic aromatic group, having an electron acceptor
group as a substituent).
17. The organic electroluminescent device according to claim 2,
wherein the hole transport layer comprises only a hole transporting
arylamine compound.
18. The organic electroluminescent device according to claim 2,
wherein the electron transport layer comprises a compound having an
anthracene ring structure represented by the following general
formula (3): ##STR00368## (wherein A.sub.1 represents a divalent
group of a substituted or unsubstituted aromatic hydrocarbon, a
divalent group of a substituted or unsubstituted aromatic
heterocyclic ring, a divalent group of a substituted or
unsubstituted condensed polycyclic aromatic, or a single bond;
B.sub.1 represents a substituted or unsubstituted aromatic
heterocyclic group; C represents a substituted or unsubstituted
aromatic hydrocarbon group, a substituted or unsubstituted aromatic
heterocyclic group, or a substituted or unsubstituted condensed
polycyclic aromatic group; D may be the same or different, and
represents a hydrogen atom, a deuterium atom, a fluorine atom, a
chlorine atom, a cyano group, a trifluoromethyl group, a linear or
branched alkyl group of 1 to 6 carbon atoms, a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group; and while p and
q maintain a relationship that the sum of p and q is 9, p
represents 7 or 8, and q represents 1 or 2).
19. The organic electroluminescent device according to claim 2,
wherein the electron transport layer comprises a compound having a
pyrimidine ring structure represented by the following general
formula (4): ##STR00369## (wherein Ar.sub.8 represents a
substituted or unsubstituted aromatic hydrocarbon group or a
substituted or unsubstituted condensed polycyclic aromatic group;
Ar.sub.9 and Ar.sub.10 may be the same or different, and represent
a hydrogen atom, a substituted or unsubstituted aromatic
hydrocarbon group, or a substituted or unsubstituted condensed
polycyclic aromatic group; and E represents a monovalent group
represented by the following structural formula (5), provided that
Ar.sub.9 and Ar.sub.10 are not simultaneously a hydrogen atom:
##STR00370## (wherein Ar.sub.11 represents a substituted or
unsubstituted aromatic heterocyclic group; R.sub.1 to R.sub.4 may
be the same or different, and represent a hydrogen atom, a
deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a
trifluoromethyl group, a linear or branched alkyl group of 1 to 6
carbon atoms, a substituted or unsubstituted aromatic hydrocarbon
group, a substituted or unsubstituted aromatic heterocyclic group,
or a substituted or unsubstituted condensed polycyclic aromatic
group).
20. The organic electroluminescent device according to claim 2,
wherein the electron transport layer comprises a compound having a
benzotriazole ring structure represented by the following general
formula (6): ##STR00371## (wherein Ar.sub.12 represents a
substituted or unsubstituted aromatic hydrocarbon group, a
substituted or unsubstituted aromatic heterocyclic group, or a
substituted or unsubstituted condensed polycyclic aromatic group;
Ar.sub.13 represents a hydrogen atom, a deuterium atom, a
substituted or unsubstituted aromatic hydrocarbon group, a
substituted or unsubstituted aromatic heterocyclic group, or a
substituted or unsubstituted condensed polycyclic aromatic group;
L.sub.1 represents a divalent group of a substituted or
unsubstituted aromatic hydrocarbon, a divalent group of a
substituted or unsubstituted aromatic heterocyclic ring, a divalent
group of a substituted or unsubstituted condensed polycyclic
aromatic, or a single bond; L.sub.2 represents a divalent group of
a substituted or unsubstituted condensed polycyclic aromatic or a
single bond; and B.sub.2 represents a substituted or unsubstituted
aromatic heterocyclic group).
Description
TECHNICAL FIELD
[0001] The present invention relates to an organic
electroluminescent device which is a preferred self-luminous device
for various display devices. Specifically, this invention relates
to organic electroluminescent devices (hereinafter referred to as
organic EL devices) using specific arylamine compounds doped with
an electron acceptor.
BACKGROUND ART
[0002] The organic EL device is a self-luminous device and has been
actively studied for their brighter, superior visibility and the
ability to display clearer images in comparison with liquid crystal
devices.
[0003] In 1987, C. W. Tang and colleagues at Eastman Kodak
developed a laminated structure device using materials assigned
with different roles, realizing practical applications of an
organic EL device with organic materials. These researchers
laminated an electron-transporting phosphor and a hole-transporting
organic substance, and injected both charges into a phosphor layer
to cause emission in order to obtain a high luminance of 1,000
cd/m.sup.2 or more at a voltage of 10 V or less (refer to Patent
Documents 1 and 2, for example).
[0004] To date, various improvements have been made for practical
applications of the organic EL device. Various roles of the
laminated structure are further subdivided to provide an
electroluminescence device that includes an anode, a hole injection
layer, a hole transport layer, a light emitting layer, an electron
transport layer, an electron injection layer, and a cathode
successively formed on a substrate, and high efficiency and
durability have been achieved by the electroluminescence device
(refer to Non-Patent Document 1, for example).
[0005] Further, there have been attempts to use triplet excitons
for further improvements of luminous efficiency, and the use of a
phosphorescence-emitting compound has been examined (refer to
Non-Patent Document 2, for example).
[0006] Devices that use light emission caused by thermally
activated delayed fluorescence (TADF) have also been developed. In
2011, Adachi et al. at Kyushu University, National University
Corporation realized 5.3% external quantum efficiency with a device
using a thermally activated delayed fluorescent material (refer to
Non-Patent Document 3, for example).
[0007] The light emitting layer can be also fabricated by doping a
charge-transporting compound generally called a host material, with
a fluorescent compound, a phosphorescence-emitting compound, or a
delayed fluorescent-emitting material. As described in the
Non-Patent Document, the selection of organic materials in an
organic EL device greatly influences various device characteristics
such as efficiency and durability (refer to Non-Patent Document 2,
for example).
[0008] In an organic EL device, charges injected from both
electrodes recombine in a light emitting layer to cause emission.
What is important here is how efficiently the hole and electron
charges are transferred to the light emitting layer in order to
form a device having excellent carrier balance. The probability of
hole-electron recombination can be improved by improving hole
injectability and electron blocking performance of blocking
injected electrons from the cathode, and high luminous efficiency
can be obtained by confining excitons generated in the light
emitting layer. The role of a hole transport material is therefore
important, and there is a need for a hole transport material that
has high hole injectability, high hole mobility, high electron
blocking performance, and high durability to electrons.
[0009] Heat resistance and amorphousness of the materials are also
important with respect to the lifetime of the device. The materials
with low heat resistance cause thermal decomposition even at a low
temperature by heat generated during the drive of the device, which
leads to the deterioration of the materials. The materials with low
amorphousness cause crystallization of a thin film even in a short
time and lead to the deterioration of the device. The materials in
use are therefore required to have characteristics of high heat
resistance and satisfactory amorphousness.
[0010] N,N'-diphenyl-N,N'-di(.alpha.-naphthyl)benzidine (NPD) and
various aromatic amine derivatives are known as the hole transport
materials used for the organic EL device (refer to Patent Documents
1 and 2, for example). Although NPD has desirable hole
transportability, its glass transition point (Tg), which is an
index of heat resistance, is as low as 96.degree. C., which causes
the degradation of device characteristics by crystallization under
a high-temperature condition (refer to Non-Patent Document 4, for
example). The aromatic amine derivatives described in the Patent
Documents include a compound known to have an excellent hole
mobility of 10.sup.-3 cm.sup.2/Vs or higher (refer to Patent
Documents 1 and 2, for example). However, since the compound is
insufficient in terms of electron blocking performance, some of the
electrons pass through the light emitting layer, and improvements
in luminous efficiency cannot be expected. For such a reason, a
material with higher electron blocking performance, a more stable
thin-film state and higher heat resistance is needed for higher
efficiency. Although an aromatic amine derivative having high
durability is reported (refer to Patent Document 3, for example),
the derivative is used as a charge transporting material used in an
electrophotographic photoconductor, and there is no example of
using the derivative in the organic EL device.
[0011] Arylamine compounds having a substituted carbazole structure
are proposed as compounds improved in the characteristics such as
heat resistance and hole injectability (refer to Patent Documents 4
and 5, for example). Further, it is proposed that hole
injectability can be improved by p-doping materials such as
trisbromophenylamine hexachloroantimony, radialene derivatives, and
F4-TCNQ into a material commonly used for the hole injection layer
or the hole transport layer (refer to Patent Document 6 and
Non-Patent Document 5). However, while the devices using these
compounds for the hole injection layer or the hole transport layer
have been improved in lower driving voltage, heat resistance,
luminous efficiency and the like, the improvements are still
insufficient. Further lower driving voltage and higher luminous
efficiency are therefore needed.
[0012] In order to improve characteristics of the organic EL device
and to improve the yield of the device production, it has been
desired to develop a device having high luminous efficiency, low
driving voltage and a long lifetime by using in combination the
materials that excel in hole and electron injection/transport
performances, stability as a thin film and durability, permitting
holes and electrons to be highly efficiently recombined
together.
[0013] Further, in order to improve characteristics of the organic
EL device, it has been desired to develop a device that maintains
carrier balance and has high efficiency, low driving voltage and a
long lifetime by using in combination the materials that excel in
hole and electron injection/transport performances, stability as a
thin film and durability.
CITATION LIST
Patent Documents
[0014] Patent Document 1: JP-A-8-048656 [0015] Patent Document 2:
Japanese Patent No. 3194657 [0016] Patent Document 3: Japanese
Patent No. 4943840 [0017] Patent Document 4: JP-A-2006-151979
[0018] Patent Document 5: WO2008/62636 [0019] Patent Document 6:
WO2014/009310 [0020] Patent Document 7: WO2005/115970 [0021] Patent
Document 8: WO2011/059000 [0022] Patent Document 9: WO2003/060956
[0023] Patent Document 10: KR-A-2013-060157 [0024] Patent Document
11: WO2013/054764
Non-Patent Documents
[0024] [0025] Non-Patent Document 1: The Japan Society of Applied
Physics, 9th Lecture Preprints, pp. 55 to 61 (2001) [0026]
Non-Patent Document 2: The Japan Society of Applied Physics, 9th
Lecture Preprints, pp. 23 to 31 (2001) [0027] Non-Patent Document
3: Appl.Phys.Let., 98, 083302 (2011) [0028] Non-Patent Document 4:
Organic EL Symposium, the 3rd Regular presentation Preprints, pp.
13 to 14 (2006) [0029] Non-Patent Document 5: Appl.Phys.Let., 89,
253506 (2006)
SUMMARY OF THE INVENTION
Problems to be Solved by the Invention
[0030] An object of the present invention is to provide an organic
EL device having high efficiency, low driving voltage and a long
lifetime, by combining various materials for an organic EL device,
which are excellent, as materials for an organic EL device having
high efficiency and high durability, in hole and electron
injection/transport performances, electron blocking ability,
stability in a thin-film state and durability, so as to allow the
respective materials to effectively reveal their
characteristics.
[0031] Physical properties of the organic compound to be provided
by the present invention include (1) good hole injection
characteristics, (2) large hole mobility, (3) excellent electron
blocking ability, (4) stability in a thin-film state, and (5)
excellent heat resistance. Physical properties of the organic EL
device to be provided by the present invention include (1) high
luminous efficiency and high power efficiency, (2) low turn on
voltage, (3) low actual driving voltage, and (4) a long
lifetime.
Means for Solving the Problems
[0032] To achieve the above object, the present inventors have
noted that an arylamine material doped with an electron acceptor is
excellent in hole injection and transport abilities, stability as a
thin film and durability, have selected a specific arylamine
compound (having a specific structure), and have produced various
organic EL devices in which a material of a hole injection layer is
doped with an electron acceptor such that holes can be efficiently
injected and transported from an anode. Then, they have intensively
conducted characteristic evaluations of the devices. Also, they
have produced various organic EL devices by combining a specific
arylamine compound (having a specific structure) doped with an
electron acceptor and a specific arylamine compound (having a
specific structure) undoped with an electron acceptor. Then, they
have intensively conducted characteristic evaluations of the
devices. As a result, they have completed the present
invention.
[0033] Specifically, according to the present invention, the
following organic EL devices are provided.
[0034] 1) An organic EL device having at least an anode, a hole
injection layer, a hole transport layer, a light emitting layer, an
electron transport layer, and a cathode in this order, wherein the
hole injection layer includes an arylamine compound represented by
the following general formula (1) and an electron acceptor.
##STR00002##
(In the formula, Ar.sub.1 to Ar.sub.4 may be the same or different,
and represent a substituted or unsubstituted aromatic hydrocarbon
group, a substituted or unsubstituted aromatic heterocyclic group,
or a substituted or unsubstituted condensed polycyclic aromatic
group.)
[0035] 2) The organic electroluminescent device according to the
above 1), wherein a layer adjacent to the light emitting layer does
not contain an electron acceptor.
[0036] 3) The organic EL device according to the above 1) or 2),
wherein the electron acceptor is an electron acceptor selected from
trisbromophenylaminehexachloroantimony, tetracyanoquinodimethane
(TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane
(F4TCNQ), and a radialene derivative.
[0037] 4) The organic EL device according to any one of the above
1) to 3), wherein the electron acceptor is a radialene derivative
represented by the following general formula (2).
##STR00003##
(In the formula, Ar.sub.5 to Ar.sub.7 may be the same or different,
and represent an aromatic hydrocarbon group, an aromatic
heterocyclic group, or a condensed polycyclic aromatic group,
having an electron acceptor group as a substituent.)
[0038] 5) The organic EL device according to any one of the above
1) to 4), wherein the hole transport layer includes only a hole
transporting arylamine compound.
[0039] 6) The organic EL device according to the above 5), wherein
the hole transport layer includes an arylamine compound represented
by the general formula (1).
[0040] 7) The organic EL device according to any one of the above
1) to 6), wherein the electron transport layer includes a compound
having an anthracene ring structure represented by the following
general formula (3).
##STR00004##
(In the formula, A.sub.1 represents a divalent group of a
substituted or unsubstituted aromatic hydrocarbon, a divalent group
of a substituted or unsubstituted aromatic heterocyclic ring, a
divalent group of a substituted or unsubstituted condensed
polycyclic aromatic, or a single bond; B.sub.1 represents a
substituted or unsubstituted aromatic heterocyclic group; C
represents a substituted or unsubstituted aromatic hydrocarbon
group, a substituted or unsubstituted aromatic heterocyclic group,
or a substituted or unsubstituted condensed polycyclic aromatic
group; D may be the same or different, and represents a hydrogen
atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano
group, a trifluoromethyl group, a linear or branched alkyl group of
1 to 6 carbon atoms, a substituted or unsubstituted aromatic
hydrocarbon group, a substituted or unsubstituted aromatic
heterocyclic group, or a substituted or unsubstituted condensed
polycyclic aromatic group; and while p and q maintain a
relationship that the sum of p and q is 9, p represents 7 or 8, and
q represents 1 or 2.)
[0041] 8) The organic EL device according to any one of the above
1) to 6), wherein the electron transport layer includes a compound
having a pyrimidine ring structure represented by the following
general formula (4).
##STR00005##
(In the formula, Ar.sub.8 represents a substituted or unsubstituted
aromatic hydrocarbon group or a substituted or unsubstituted
condensed polycyclic aromatic group; Ar.sub.9 and Ar.sub.10 may be
the same or different, and represent a hydrogen atom, a substituted
or unsubstituted aromatic hydrocarbon group, or a substituted or
unsubstituted condensed polycyclic aromatic group; and E represents
a monovalent group represented by the following structural formula
(5), provided that Ar.sub.9 and Ar.sub.10 are not simultaneously a
hydrogen atom.
##STR00006##
(In the formula, Ar.sub.11 represents a substituted or
unsubstituted aromatic heterocyclic group; R.sub.1 to R.sub.4 may
be the same or different, and represent a hydrogen atom, a
deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a
trifluoromethyl group, a linear or branched alkyl group of 1 to 6
carbon atoms, a substituted or unsubstituted aromatic hydrocarbon
group, a substituted or unsubstituted aromatic heterocyclic group,
or a substituted or unsubstituted condensed polycyclic aromatic
group.)
[0042] 9) The organic EL device according to any one of the above
1) to 6), wherein the electron transport layer includes a compound
having a benzotriazole ring structure represented by the following
general formula (6).
##STR00007##
(In the formula, Ar.sub.12 represents a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group; Ar.sub.13
represents a hydrogen atom, a deuterium atom, a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group; L.sub.1
represents a divalent group of a substituted or unsubstituted
aromatic hydrocarbon, a divalent group of a substituted or
unsubstituted aromatic heterocyclic ring, a divalent group of a
substituted or unsubstituted condensed polycyclic aromatic, or a
single bond; L.sub.2 represents a divalent group of a substituted
or unsubstituted condensed polycyclic aromatic or a single bond;
and B.sub.2 represents a substituted or unsubstituted aromatic
heterocyclic group.)
[0043] 10) The organic EL device according to any one of the above
1) to 9), wherein the light emitting layer includes a blue light
emitting dopant.
[0044] 11) The organic EL device according to the above 10),
wherein the light emitting layer includes a blue light emitting
dopant which is a pyrene derivative.
[0045] 12) The organic EL device according to the above 10),
wherein the blue light emitting dopant includes a light emitting
dopant which is an amine derivative having a condensed ring
structure represented by the following general formula (7).
##STR00008##
(In the formula, A.sub.2 represents a divalent group of a
substituted or unsubstituted aromatic hydrocarbon, a divalent group
of a substituted or unsubstituted aromatic heterocyclic ring, a
divalent group of a substituted or unsubstituted condensed
polycyclic aromatic, or a single bond; Ar.sub.14 and Ar.sub.15 may
be the same or different, and represent a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group, and may bind to
each other via a single bond, a substituted or unsubstituted
methylene group, an oxygen atom, or a sulfur atom to form a ring;
R.sub.5 to R.sub.8 may be the same or different, and represent a
hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom,
a cyano group, a nitro group, a linear or branched alkyl group of 1
to 6 carbon atoms that may have a substituent, a cycloalkyl group
of 5 to 10 carbon atoms that may have a substituent, a linear or
branched alkenyl group of 2 to 6 carbon atoms that may have a
substituent, a linear or branched alkyloxy group of 1 to 6 carbon
atoms that may have a substituent, a cycloalkyloxy group of 5 to 10
carbon atoms that may have a substituent, a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, a substituted or
unsubstituted condensed polycyclic aromatic group, a substituted or
unsubstituted aryloxy group, or a disubstituted amino group
substituted with a group selected from an aromatic hydrocarbon
group, an aromatic heterocyclic group, or a condensed polycyclic
aromatic group, where the respective groups may bind to each other
via a single bond, a substituted or unsubstituted methylene group,
an oxygen atom, or a sulfur atom to form a ring, or may bind to the
benzene ring to which R.sub.5 to R.sub.8 bind via a substituted or
unsubstituted methylene group, an oxygen atom, a sulfur atom, or a
monosubstituted amino group to form a ring; R.sub.9 to R.sub.11 may
be the same or different, and represent a hydrogen atom, a
deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a
nitro group, a linear or branched alkyl group of 1 to 6 carbon
atoms that may have a substituent, a cycloalkyl group of 5 to 10
carbon atoms that may have a substituent, a linear or branched
alkenyl group of 2 to 6 carbon atoms that may have a substituent, a
linear or branched alkyloxy group of 1 to 6 carbon atoms that may
have a substituent, a cycloalkyloxy group of 5 to 10 carbon atoms
that may have a substituent, a substituted or unsubstituted
aromatic hydrocarbon group, a substituted or unsubstituted aromatic
heterocyclic group, a substituted or unsubstituted condensed
polycyclic aromatic group, or a substituted or unsubstituted
aryloxy group, where the respective groups may bind to each other
via a single bond, a substituted or unsubstituted methylene group,
an oxygen atom, or a sulfur atom to form a ring, or may bind to the
benzene ring to which R.sub.9 to R.sub.11 bind via a substituted or
unsubstituted methylene group, an oxygen atom, a sulfur atom, or a
monosubstituted amino group to form a ring; and R.sub.12 and
R.sub.13 may be the same or different, and represent a linear or
branched alkyl group of 1 to 6 carbon atoms that may have a
substituent, a cycloalkyl group of 5 to 10 carbon atoms that may
have a substituent, a linear or branched alkenyl group of 2 to 6
carbon atoms that may have a substituent, a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, a substituted or
unsubstituted condensed polycyclic aromatic group, or a substituted
or unsubstituted aryloxy group, where the respective groups may
bind to each other via a single bond, a substituted or
unsubstituted methylene group, an oxygen atom, a sulfur atom, or a
monosubstituted amino group to form a ring.)
[0046] 13) The organic EL device according to any one of the above
1) to 12), wherein the light emitting layer includes an anthracene
derivative.
[0047] 14) The organic EL device according to the above 13),
wherein the light emitting layer includes a host material which is
an anthracene derivative.
[0048] Specific examples of the "aromatic hydrocarbon group", the
"aromatic heterocyclic group", or the "condensed polycyclic
aromatic group" in the "substituted or unsubstituted aromatic
hydrocarbon group", the "substituted or unsubstituted aromatic
heterocyclic group", or the "substituted or unsubstituted condensed
polycyclic aromatic group" represented by Ar.sub.1 to Ar.sub.4 in
the general formula (1) include a phenyl group, a biphenylyl group,
a terphenylyl group, a naphthyl group, an anthracenyl group, a
phenanthrenyl group, a fluorenyl group, an indenyl group, a pyrenyl
group, a perylenyl group, a fluoranthenyl group, a triphenylenyl
group, a pyridyl group, a pyrimidinyl group, a triazinyl group, a
furyl group, a pyrrolyl group, a thienyl group, a quinolyl group,
an isoquinolyl group, a benzofuranyl group, a benzothienyl group,
an indolyl group, a carbazolyl group, a benzoxazolyl group, a
benzothiazolyl group, a quinoxalinyl group, a benzoimidazolyl
group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl
group, a naphthyridinyl group, a phenanthrolinyl group, an
acridinyl group, and a carbolinyl group.
[0049] Specific examples of the "substituent" in the "substituted
aromatic hydrocarbon group", the "substituted aromatic heterocyclic
group", or the "substituted condensed polycyclic aromatic group"
represented by Ar.sub.1 to Ar.sub.4 in the general formula (1)
include a deuterium atom, a cyano group, a nitro group; halogen
atoms such as a fluorine atom, a chlorine atom, a bromine atom, and
an iodine atom; linear or branched alkyl groups of 1 to 6 carbon
atoms such as a methyl group, an ethyl group, an n-propyl group, an
isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl
group, an n-pentyl group, an isopentyl group, a neopentyl group,
and an n-hexyl group; linear or branched alkyloxy groups of 1 to 6
carbon atoms such as a methyloxy group, an ethyloxy group, and a
propyloxy group; alkenyl groups such as a vinyl group and an allyl
group; aryloxy groups such as a phenyloxy group and a tolyloxy
group; arylalkyloxy groups such as a benzyloxy group and a
phenethyloxy group; aromatic hydrocarbon groups or condensed
polycyclic aromatic groups such as a phenyl group, a biphenylyl
group, a terphenylyl group, a naphthyl group, an anthracenyl group,
a phenanthrenyl group, a fluorenyl group, an indenyl group, a
pyrenyl group, a perylenyl group, a fluoranthenyl group, and a
triphenylenyl group; aromatic heterocyclic groups such as a pyridyl
group, a pyrimidinyl group, a triazinyl group, a thienyl group, a
furyl group, a pyrrolyl group, a quinolyl group, an isoquinolyl
group, a benzofuranyl group, a benzothienyl group, an indolyl
group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl
group, a quinoxalinyl group, a benzoimidazolyl group, a pyrazolyl
group, a dibenzofuranyl group, a dibenzothienyl group, and a
carbolinyl group; arylvinyl groups such as a styryl group and a
naphthylvinyl group; acyl groups such as an acetyl group and a
benzoyl group; and other groups, and these substituents may be
further substituted with a substituent exemplified above. Further,
these substituents may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring.
[0050] Examples of the "electron acceptor group" in the "aromatic
hydrocarbon group, the aromatic heterocyclic group, or the
condensed polycyclic aromatic group, having an electron acceptor
group as a substitutent" represented by Ar.sub.5 to Ar.sub.7 in the
general formula (2) include a fluorine atom, a chlorine atom, a
bromine atom, a cyano group, a trifluoromethyl group, and a nitro
group.
[0051] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "aromatic hydrocarbon group, the aromatic heterocyclic
group, or the condensed polycyclic aromatic group, having an
electron acceptor group as a substitutent" represented by Ar.sub.5
to Ar.sub.7 in the general formula (2) include the same groups
exemplified as the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by Ar.sub.1 to Ar.sub.4 in the above general
formula (1).
[0052] Further, these groups may have a substituent other than the
electron acceptor group, and specific examples of the substituent
include a deuterium atom; aromatic hydrocarbon groups or condensed
polycyclic aromatic groups such as a phenyl group, a biphenylyl
group, a terphenylyl group, a naphthyl group, an anthracenyl group,
a phenanthrenyl group, a fluorenyl group, an indenyl group, a
pyrenyl group, a perylenyl group, a fluoranthenyl group, and a
triphenylenyl group; and aromatic heterocyclic groups such as a
pyridyl group, a pyrimidinyl group, a triazinyl group, a thienyl
group, a furyl group, a pyrrolyl group, a quinolyl group, an
isoquinolyl group, a benzofuranyl group, a benzothienyl group, an
indolyl group, a carbazolyl group, a benzoxazolyl group, a
benzothiazolyl group, a quinoxalinyl group, a benzoimidazolyl
group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl
group, and a carbolinyl group, and these substituents may be
further substituted with a substituent exemplified above or an
electron acceptor group. Then, these substituents may bind to each
other via a single bond, a substituted or unsubstituted methylene
group, an oxygen atom, or a sulfur atom to form a ring.
[0053] Specific examples of the "aromatic hydrocarbon", the
"aromatic heterocyclic ring", or the "condensed polycyclic
aromatic" of the "substituted or unsubstituted aromatic
hydrocarbon", the "substituted or unsubstituted aromatic
heterocyclic ring", or the "substituted or unsubstituted condensed
polycyclic aromatic" in the "divalent group of a substituted or
unsubstituted aromatic hydrocarbon", the "divalent group of a
substituted or unsubstituted aromatic heterocyclic ring", or the
"divalent group of a substituted or unsubstituted condensed
polycyclic aromatic" represented by A.sub.1 in the general formula
(3) include benzene, biphenyl, terphenyl, tetrakisphenyl, styrene,
naphthalene, anthracene, acenaphthalene, fluorene, phenanthrene,
indane, pyrene, triphenylene, pyridine, pyrimidine, triazine,
pyrrole, furan, thiophene, quinoline, isoquinoline, benzofuran,
benzothiophene, indoline, carbazole, carboline, benzoxazole,
benzothiazole, quinoxaline, benzimidazole, pyrazole, dibenzofuran,
dibenzothiophene, naphthyridine, phenanthroline, and acridine.
[0054] Then, the "divalent group of a substituted or unsubstituted
aromatic hydrocarbon", the "divalent group of a substituted or
unsubstituted aromatic heterocyclic ring", or the "divalent group
of a substituted or unsubstituted condensed polycyclic aromatic"
represented by A.sub.1 in the general formula (3) represents a
divalent group that results from the removal of two hydrogen atoms
from the above "aromatic hydrocarbon", "aromatic heterocyclic
ring", or "condensed polycyclic aromatic".
[0055] Further, these divalent groups may have a substituent, and
examples of the substituent include the same substituents
exemplified as the "substituent" in the "substituted aromatic
hydrocarbon group", the "substituted aromatic heterocyclic group",
or the "substituted condensed polycyclic aromatic group"
represented by Ar.sub.1 to Ar.sub.4 in the above general formula
(1), and possible embodiments may also be the same embodiments as
the exemplified embodiments.
[0056] Specific examples of the "aromatic heterocyclic group" in
the "substituted or unsubstituted aromatic heterocyclic group"
represented by B.sub.1 in the general formula (3) include a
triazinyl group, a pyridyl group, a pyrimidinyl group, a furyl
group, a pyrrolyl group, a thienyl group, a quinolyl group, an
isoquinolyl group, a benzofuranyl group, a benzothienyl group, an
indolyl group, a carbazolyl group, a carbolinyl group, a
benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a
benzoimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a
dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl
group, an acridinyl group, and a carbolinyl group.
[0057] Specific examples of the "substituent" in the "substituted
aromatic heterocyclic group" represented by B.sub.1 in the general
formula (3) include a deuterium atom, a cyano group, a nitro group;
halogen atoms such as a fluorine atom, a chlorine atom, a bromine
atom, and an iodine atom; linear or branched alkyl groups of 1 to 6
carbon atoms such as a methyl group, an ethyl group, an n-propyl
group, an isopropyl group, an n-butyl group, an isobutyl group, a
tert-butyl group, an n-pentyl group, an isopentyl group, a
neopentyl group, and an n-hexyl group; cycloalkyl groups of 5 to 10
carbon atoms such as a cyclopentyl group, a cyclohexyl group, a
1-adamantyl group, and a 2-adamantyl group; linear or branched
alkyloxy groups of 1 to 6 carbon atoms such as a methyloxy group,
an ethyloxy group, and a propyloxy group; cycloalkyloxy groups of 5
to 10 carbon atoms such as a cyclopentyloxy group, a cyclohexyloxy
group, a 1-adamantyloxy group, and a 2-adamantyloxy group; alkenyl
groups such as a vinyl group and an allyl group; aryloxy groups
such as a phenyloxy group and a tolyloxy group; arylalkyloxy groups
such as a benzyloxy group and a phenethyloxy group; aromatic
hydrocarbon groups or condensed polycyclic aromatic groups such as
a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl
group, an anthracenyl group, a phenanthrenyl group, a fluorenyl
group, an indenyl group, a pyrenyl group, a perylenyl group, a
fluoranthenyl group, and a triphenylenyl group; aromatic
heterocyclic groups such as a pyridyl group, a pyrimidinyl group, a
triazinyl group, a thienyl group, a furyl group, a pyrrolyl group,
a quinolyl group, an isoquinolyl group, a benzofuranyl group, a
benzothienyl group, an indolyl group, a carbazolyl group, a
benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a
benzoimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a
dibenzothienyl group, and a carbolinyl group; aryloxy groups such
as a phenyloxy group, a biphenylyloxy group, a naphthyloxy group,
an anthracenyloxy group, and a phenanthrenyloxy group; arylvinyl
groups such as a styryl group and a naphthylvinyl group; acyl
groups such as an acetyl group and a benzoyl group; and other
groups, and these substituents may be further substituted with a
substituent exemplified above. Further, these substituents may bind
to each other via a single bond, a substituted or unsubstituted
methylene group, an oxygen atom, or a sulfur atom to form a
ring.
[0058] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by C in the general formula (3) include the same
groups exemplified as the "aromatic hydrocarbon group", the
"aromatic heterocyclic group", or the "condensed polycyclic
aromatic group" in the "substituted or unsubstituted aromatic
hydrocarbon group", the "substituted or unsubstituted aromatic
heterocyclic group", or the "substituted or unsubstituted condensed
polycyclic aromatic group" represented by Ar.sub.1 to Ar.sub.4 in
the above general formula (1), and when a plurality of these groups
bind to the same anthracene ring (when q is 2), these groups may be
the same or different.
[0059] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0060] Specific examples of the "linear or branched alkyl group of
1 to 6 carbon atoms" represented by D in the general formula (3)
include a methyl group, an ethyl group, an n-propyl group, an
isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl
group, an n-pentyl group, an isopentyl group, a neopentyl group,
and an n-hexyl group.
[0061] Further, the plurality of D may be the same or different,
and these groups may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring.
[0062] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by D in the general formula (3) include the same
groups exemplified as the "aromatic hydrocarbon group", the
"aromatic heterocyclic group", or the "condensed polycyclic
aromatic group" in the "substituted or unsubstituted aromatic
hydrocarbon group", the "substituted or unsubstituted aromatic
heterocyclic group", or the "substituted or unsubstituted condensed
polycyclic aromatic group" represented by Ar.sub.1 to Ar.sub.4 in
the above general formula (1), and the plurality of D may be the
same or different, and these groups may bind to each other via a
single bond, a substituted or unsubstituted methylene group, an
oxygen atom, or a sulfur atom to form a ring.
[0063] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0064] Specific examples of the "aromatic hydrocarbon group" or the
"condensed polycyclic aromatic group" in the "substituted or
unsubstituted aromatic hydrocarbon group" or the "substituted or
unsubstituted condensed polycyclic aromatic group" represented by
Ar.sub.8, Ar.sub.9, and Ar.sub.10 in the general formula (4)
include groups such as a phenyl group, a biphenylyl group, a
terphenylyl group, a tetrakisphenyl group, a styryl group, a
naphthyl group, an anthracenyl group, an acenaphthenyl group, a
phenanthrenyl group, a fluorenyl group, an indenyl group, a pyrenyl
group, a perylenyl group, a fluoranthenyl group, and a
triphenylenyl group.
[0065] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0066] Specific examples of the "aromatic heterocyclic group" in
the "substituted or unsubstituted aromatic heterocyclic group"
represented by Ar.sub.11 in the structural formula (5) include
groups such as a triazinyl group, a pyridyl group, a pyrimidinyl
group, a furyl group, a pyrrolyl group, a thienyl group, a quinolyl
group, an isoquinolyl group, a benzofuranyl group, a benzothienyl
group, an indolyl group, a carbazolyl group, a benzoxazolyl group,
a benzothiazolyl group, a quinoxalinyl group, a benzoimidazolyl
group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl
group, a naphthyridinyl group, a phenanthrolinyl group, an
acridinyl group, and a carbolinyl group.
[0067] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0068] Specific examples of the "linear or branched alkyl group of
1 to 6 carbon atoms" represented by R.sub.1 to R.sub.4 in the
structural formula (5) include a methyl group, an ethyl group, an
n-propyl group, an i-propyl group, an n-butyl group, a
2-methylpropyl group, a tert-butyl group, an n-pentyl group, a
3-methylbutyl group, a tert-pentyl group, an n-hexyl group, an
iso-hexyl group, and a tert-hexyl group.
[0069] Specific examples of the "aromatic hydrocarbon group", the
"aromatic heterocyclic group", or the "condensed polycyclic
aromatic group" in the "substituted or unsubstituted aromatic
hydrocarbon group", the "substituted or unsubstituted aromatic
heterocyclic group", or the "substituted or unsubstituted condensed
polycyclic aromatic group" represented by R.sub.1 to R.sub.4 in the
structural formula (5) include groups such as a phenyl group, a
biphenylyl group, a terphenylyl group, a tetrakisphenyl group, a
styryl group, a naphthyl group, an anthracenyl group, an
acenaphthenyl group, a phenanthrenyl group, a fluorenyl group, an
indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl
group, a triphenylenyl group, a triazinyl group, a pyridyl group, a
pyrimidinyl group, a furyl group, a pyrrolyl group, a thienyl
group, a quinolyl group, an isoquinolyl group, a benzofuranyl
group, a benzothienyl group, an indolyl group, a carbazolyl group,
a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group,
a benzoimidazolyl group, a pyrazolyl group, a dibenzofuranyl group,
a dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl
group, an acridinyl group, and a carbolinyl group.
[0070] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0071] Specific examples of the "aromatic hydrocarbon group", the
"aromatic heterocyclic group", or the "condensed polycyclic
aromatic group" in the "substituted or unsubstituted aromatic
hydrocarbon group", the "substituted or unsubstituted aromatic
heterocyclic group", or the "substituted or unsubstituted condensed
polycyclic aromatic group" represented by Ar.sub.12 and Ar.sub.13
in the general formula (6) include groups such as a phenyl group, a
biphenylyl group, a terphenylyl group, a tetrakisphenyl group, a
styryl group, a naphthyl group, an anthracenyl group, an
acenaphthenyl group, a phenanthrenyl group, a fluorenyl group, an
indenyl group, a pyrenyl group, a pyridyl group, a triazinyl group,
a pyrimidinyl group, a furyl group, a pyrrolyl group, a thienyl
group, a quinolyl group, an isoquinolyl group, a benzofuranyl
group, a benzothienyl group, an indolyl group, a carbazolyl group,
a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group,
a benzoimidazolyl group, a pyrazolyl group, a dibenzofuranyl group,
a dibenzothienyl group, a naphthyridinyl group, a phenanthrolinyl
group, and an acridinyl group.
[0072] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0073] Specific examples of the "aromatic hydrocarbon", the
"aromatic heterocyclic ring", or the "condensed polycyclic
aromatic" of the "substituted or unsubstituted aromatic
hydrocarbon", the "substituted or unsubstituted aromatic
heterocyclic ring", or the "substituted or unsubstituted condensed
polycyclic aromatic" in the "divalent group of a substituted or
unsubstituted aromatic hydrocarbon", the "divalent group of a
substituted or unsubstituted aromatic heterocyclic ring", or the
"divalent group of a substituted or unsubstituted condensed
polycyclic aromatic" represented by L.sub.1 in the general formula
(6) include benzene, biphenyl, terphenyl, tetrakisphenyl, styrene,
naphthalene, anthracene, acenaphthalene, fluorene, phenanthrene,
indane, pyrene, triphenylene, pyridine, bipyridine, pyrimidine,
triazine, pyrrole, furan, thiophene, quinoline, isoquinoline,
benzofuran, benzothiophene, indoline, carbazole, carboline,
benzoxazole, benzothiazole, quinoxaline, benzimidazole, pyrazole,
dibenzofuran, dibenzothiophene, naphthyridine, phenanthroline, and
acridine.
[0074] Then, the "divalent group of a substituted or unsubstituted
aromatic hydrocarbon", the "divalent group of a substituted or
unsubstituted aromatic heterocyclic ring", or the "divalent group
of a substituted or unsubstituted condensed polycyclic aromatic"
represented by L.sub.1 in the general formula (6) represents a
divalent group that results from the removal of two hydrogen atoms
from the above "aromatic hydrocarbon", "aromatic heterocyclic
ring", or "condensed polycyclic aromatic".
[0075] Further, these divalent groups may have a substituent, and
examples of the substituent include the same substituents
exemplified as the "substituent" in the "substituted aromatic
hydrocarbon group", the "substituted aromatic heterocyclic group",
or the "substituted condensed polycyclic aromatic group"
represented by Ar.sub.1 to Ar.sub.4 in the above general formula
(1), and possible embodiments may also be the same embodiments as
the exemplified embodiments.
[0076] Specific examples of the "condensed polycyclic aromatic" of
the "substituted or unsubstituted condensed polycyclic aromatic" in
the "divalent group of a substituted or unsubstituted condensed
polycyclic aromatic" represented by L.sub.2 in the general formula
(6) include naphthalene, anthracene, acenaphthalene, fluorene,
phenanthrene, indane, pyrene, and triphenylene.
[0077] Then, the "divalent group of a substituted or unsubstituted
condensed polycyclic aromatic" represented by L.sub.2 in the
general formula (6) represents a divalent group that results from
the removal of two hydrogen atoms from the above "condensed
polycyclic aromatic".
[0078] Further, these divalent groups may have a substituent, and
examples of the substituent include the same substituents
exemplified as the "substituent" in the "substituted aromatic
hydrocarbon group", the "substituted aromatic heterocyclic group",
or the "substituted condensed polycyclic aromatic group"
represented by Ar.sub.1 to Ar.sub.4 in the above general formula
(1), and possible embodiments may also be the same embodiments as
the exemplified embodiments.
[0079] Specific examples of the "aromatic heterocyclic group", in
the "substituted or unsubstituted aromatic heterocyclic group"
represented by B.sub.2 in the general formula (6) include groups
such as a pyridyl group, a bipyridyl group, a triazinyl group, a
pyrimidinyl group, a furyl group, a pyrrolyl group, a thienyl
group, a quinolyl group, an isoquinolyl group, a benzofuranyl
group, a benzothienyl group, an indolyl group, a carbazolyl group,
a carbolinyl group, a benzoxazolyl group, a benzothiazolyl group, a
quinoxalinyl group, a benzoimidazolyl group, a pyrazolyl group, a
dibenzofuranyl group, a dibenzothienyl group, a naphthyridinyl
group, a phenanthrolinyl group, and an acridinyl group.
[0080] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic heterocyclic group"
represented by B.sub.1 in the above general formula (3), and
possible embodiments may also be the same embodiments as the
exemplified embodiments.
[0081] Examples of the "aromatic hydrocarbon", the "aromatic
heterocyclic ring", or the "condensed polycyclic aromatic" of the
"substituted or unsubstituted aromatic hydrocarbon", the
"substituted or unsubstituted aromatic heterocyclic ring", or the
"substituted or unsubstituted condensed polycyclic aromatic" in the
"divalent group of a substituted or unsubstituted aromatic
hydrocarbon", the "divalent group of a substituted or unsubstituted
aromatic heterocyclic ring", or the "divalent group of a
substituted or unsubstituted condensed polycyclic aromatic"
represented by A.sub.2 in the general formula (7) include the same
groups exemplified as the "aromatic hydrocarbon", the "aromatic
heterocyclic ring", or the "condensed polycyclic aromatic" of the
"substituted or unsubstituted aromatic hydrocarbon", the
"substituted or unsubstituted aromatic heterocyclic ring", or the
"substituted or unsubstituted condensed polycyclic aromatic" in the
"divalent group of a substituted or unsubstituted aromatic
hydrocarbon", the "divalent group of a substituted or unsubstituted
aromatic heterocyclic ring", or the "divalent group of a
substituted or unsubstituted condensed polycyclic aromatic"
represented by A.sub.1 in the above general formula (3).
[0082] Then, the "divalent group of a substituted or unsubstituted
aromatic hydrocarbon", the "divalent group of a substituted or
unsubstituted aromatic heterocyclic ring", or the "divalent group
of a substituted or unsubstituted condensed polycyclic aromatic"
represented by A.sub.2 in the general formula (7) represents a
divalent group that results from the removal of two hydrogen atoms
from the above "aromatic hydrocarbon", "aromatic heterocyclic
ring", or "condensed polycyclic aromatic".
[0083] Further, these divalent groups may have a substituent, and
examples of the substituent include the same substituents
exemplified as the "substituent" in the "substituted aromatic
hydrocarbon group", the "substituted aromatic heterocyclic group",
or the "substituted condensed polycyclic aromatic group"
represented by Ar.sub.1 to Ar.sub.4 in the above general formula
(1), and possible embodiments may also be the same embodiments as
the exemplified embodiments.
[0084] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by Ar.sub.14 and Ar.sub.15 in the general
formula (7) include the same groups exemplified as the "aromatic
hydrocarbon group", the "aromatic heterocyclic group", or the
"condensed polycyclic aromatic group" in the "substituted or
unsubstituted aromatic hydrocarbon group", the "substituted or
unsubstituted aromatic heterocyclic group", or the "substituted or
unsubstituted condensed polycyclic aromatic group" represented by
Ar.sub.1 to Ar.sub.4 in the above general formula (1), and
Ar.sub.14 and Ar.sub.15 may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring.
[0085] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0086] Specific examples of the "linear or branched alkyl group of
1 to 6 carbon atoms", the "cycloalkyl group of 5 to 10 carbon
atoms", or the "linear or branched alkenyl group of 2 to 6 carbon
atoms" in the "linear or branched alkyl group of 1 to 6 carbon
atoms that may have a substituent", the "cycloalkyl group of 5 to
10 carbon atoms that may have a substituent", or the "linear or
branched alkenyl group of 2 to 6 carbon atoms that may have a
substituent" represented by R.sub.5 to R.sub.11 in the general
formula (7) include a methyl group, an ethyl group, an n-propyl
group, an isopropyl group, an n-butyl group, an isobutyl group, a
tert-butyl group, an n-pentyl group, an isopentyl group, a
neopentyl group, an n-hexyl group, a cyclopentyl group, a
cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a vinyl
group, an allyl group, an isopropenyl group, and a 2-butenyl group,
and these groups may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring, or these groups (R.sub.5 to R.sub.11)
may bind to the benzene ring to which these groups (R.sub.5 to
R.sub.11) directly bind via a linking group such as a substituted
or unsubstituted methylene group, an oxygen atom, a sulfur atom, or
a monosubstituted amino group to form a ring.
[0087] Specific examples of the "substituent" in the "linear or
branched alkyl group of 1 to 6 carbon atoms that has a
substituent", the "cycloalkyl group of 5 to 10 carbon atoms that
has a substituent", or the "linear or branched alkenyl group of 2
to 6 carbon atoms that has a substituent" represented by R.sub.5 to
R.sub.11 in the general formula (7) include a deuterium atom, a
cyano group, a nitro group; halogen atoms such as a fluorine atom,
a chlorine atom, a bromine atom, and an iodine atom; linear or
branched alkyloxy groups of 1 to 6 carbon atoms such as a methyloxy
group, an ethyloxy group, and a propyloxy group; alkenyl groups
such as a vinyl group and an allyl group; aryloxy groups such as a
phenyloxy group and a tolyloxy group; arylalkyloxy groups such as a
benzyloxy group and a phenethyloxy group; aromatic hydrocarbon
groups or condensed polycyclic aromatic groups such as a phenyl
group, a biphenylyl group, a terphenylyl group, a naphthyl group,
an anthracenyl group, a phenanthrenyl group, a fluorenyl group, an
indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl
group, and a triphenylenyl group; aromatic heterocyclic groups such
as a pyridyl group, a pyrimidinyl group, a triazinyl group, a
thienyl group, a furyl group, a pyrrolyl group, a quinolyl group,
an isoquinolyl group, a benzofuranyl group, a benzothienyl group,
an indolyl group, a carbazolyl group, a benzoxazolyl group, a
benzothiazolyl group, a quinoxalinyl group, a benzoimidazolyl
group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl
group, and a carbolinyl group; disubstituted amino groups
substituted with an aromatic hydrocarbon group or a condensed
polycyclic aromatic group such as a diphenylamino group and a
dinaphthylamino group; disubstituted amino groups substituted with
an aromatic heterocyclic group such as a dipyridylamino group and a
dithienylamino group; disubstituted amino groups substituted with a
substituent selected from an aromatic hydrocarbon group, a
condensed polycyclic aromatic group, or an aromatic heterocyclic
group; and other groups, and these substituents may be further
substituted with a substituent exemplified above. Further, these
substituents may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring.
[0088] Specific examples of the "linear or branched alkyloxy group
of 1 to 6 carbon atoms" or the "cycloalkyloxy group of 5 to 10
carbon atoms" in the "linear or branched alkyloxy group of 1 to 6
carbon atoms that may have a substituent" or the "cycloalkyloxy
group of 5 to 10 carbon atoms that may have a substituent"
represented by R.sub.5 to R.sub.11 in the general formula (7)
include a methyloxy group, an ethyloxy group, an n-propyloxy group,
an isopropyloxy group, an n-butyloxy group, a tert-butyloxy group,
an n-pentyloxy group, an n-hexyloxy group, a cyclopentyloxy group,
a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy
group, a 1-adamantyloxy group, and a 2-adamantyloxy group, and
these groups may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring, or these groups (R.sub.5 to R.sub.11)
may bind to the benzene ring to which these groups (R.sub.5 to
R.sub.11) directly bind via a linking group such as a substituted
or unsubstituted methylene group, an oxygen atom, a sulfur atom, or
a monosubstituted amino group to form a ring.
[0089] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "linear or branched alkyl group of 1 to 6
carbon atoms that has a substituent", the "cycloalkyl group of 5 to
10 carbon atoms that has a substituent", or the "linear or branched
alkenyl group of 2 to 6 carbon atoms that has a substituent"
represented by R.sub.5 to R.sub.11 in the above general formula
(7), and possible embodiments may also be the same embodiments as
the exemplified embodiments.
[0090] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by R.sub.5 to R.sub.11 in the general formula
(7) include the same groups exemplified as the "aromatic
hydrocarbon group", the "aromatic heterocyclic group", or the
"condensed polycyclic aromatic group" in the "substituted or
unsubstituted aromatic hydrocarbon group", the "substituted or
unsubstituted aromatic heterocyclic group", or the "substituted or
unsubstituted condensed polycyclic aromatic group" represented by
Ar.sub.1 to Ar.sub.4 in the above general formula (1), and these
groups may bind to each other via a single bond, a substituted or
unsubstituted methylene group, an oxygen atom, or a sulfur atom to
form a ring, or these groups (R.sub.5 to R.sub.11) may bind to the
benzene ring to which these groups (R.sub.5 to R.sub.11) directly
bind via a linking group such as a substituted or unsubstituted
methylene group, an oxygen atom, a sulfur atom, or a
monosubstituted amino group to form a ring.
[0091] Specific examples of the "substituent" in the "substituted
aromatic hydrocarbon group", the "substituted aromatic heterocyclic
group", or the "substituted condensed polycyclic aromatic group"
represented by R.sub.5 to R.sub.11 in the general formula (7)
include a deuterium atom, a cyano group, a nitro group; halogen
atoms such as a fluorine atom, a chlorine atom, a bromine atom, and
an iodine atom; linear or branched alkyl groups of 1 to 6 carbon
atoms such as a methyl group, an ethyl group, an n-propyl group, an
isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl
group, an n-pentyl group, an isopentyl group, a neopentyl group,
and an n-hexyl group; linear or branched alkyloxy groups of 1 to 6
carbon atoms such as a methyloxy group, an ethyloxy group, and a
propyloxy group; alkenyl groups such as a vinyl group and an allyl
group; aryloxy groups such as a phenyloxy group and a tolyloxy
group; arylalkyloxy groups such as a benzyloxy group and a
phenethyloxy group; aromatic hydrocarbon groups or condensed
polycyclic aromatic groups such as a phenyl group, a biphenylyl
group, a terphenylyl group, a naphthyl group, an anthracenyl group,
a phenanthrenyl group, a fluorenyl group, an indenyl group, a
pyrenyl group, a perylenyl group, a fluoranthenyl group, and a
triphenylenyl group; aromatic heterocyclic groups such as a pyridyl
group, a pyrimidinyl group, a triazinyl group, a thienyl group, a
furyl group, a pyrrolyl group, a quinolyl group, an isoquinolyl
group, a benzofuranyl group, a benzothienyl group, an indolyl
group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl
group, a quinoxalinyl group, a benzoimidazolyl group, a pyrazolyl
group, a dibenzofuranyl group, a dibenzothienyl group, and a
carbolinyl group; arylvinyl groups such as a styryl group and a
naphthylvinyl group; acyl groups such as an acetyl group and a
benzoyl group; silyl groups such as a trimethylsilyl group and a
triphenylsilyl group; disubstituted amino groups substituted with
an aromatic hydrocarbon group or a condensed polycyclic aromatic
group such as a diphenylamino group and a dinaphthylamino group;
disubstituted amino groups substituted with an aromatic
heterocyclic group such as a dipyridylamino group and a
dithienylamino group; disubstituted amino groups substituted with a
substituent selected from an aromatic hydrocarbon group, a
condensed polycyclic aromatic group, or an aromatic heterocyclic
group; and other groups, and these substituents may be further
substituted with a substituent exemplified above. Further, these
substituents may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring.
[0092] Specific examples of the "aryloxy group" in the "substituted
or unsubstituted aryloxy group" represented by R.sub.5 to R.sub.11
in the general formula (7) include a phenyloxy group, a
biphenylyloxy group, a terphenylyloxy group, a naphthyloxy group,
an anthracenyloxy group, a phenanthrenyloxy group, a fluorenyloxy
group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy
group, and these groups may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring, or these groups (R.sub.5 to R.sub.11)
may bind to the benzene ring to which these groups (R.sub.5 to
R.sub.11) directly bind via a linking group such as a substituted
or unsubstituted methylene group, an oxygen atom, a sulfur atom, or
a monosubstituted amino group to form a ring.
[0093] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by R.sub.5 to
R.sub.11 in the above general formula (7), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0094] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "disubstituted amino group substituted with a group selected
from an aromatic hydrocarbon group, an aromatic heterocyclic group,
or a condensed polycyclic aromatic group" represented by R.sub.5 to
R.sub.8 in the general formula (7) include the same groups
exemplified as the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by Ar.sub.1 to Ar.sub.4 in the above general
formula (1).
[0095] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by R.sub.5 to
R.sub.8 in the above general formula (7), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0096] In the case of the "disubstituted amino group substituted
with a group selected from an aromatic hydrocarbon group, an
aromatic heterocyclic group, or a condensed polycyclic aromatic
group" represented by R.sub.5 to R.sub.8 in the general formula
(7), these groups (R.sub.5 to R.sub.8) may bind to each other
through the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
included in these groups (R.sub.5 to R.sub.8) via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring, or these groups (R.sub.5 to R.sub.8)
may bind to the benzene ring to which these groups (R.sub.5 to
R.sub.8) directly bind through the "aromatic hydrocarbon group",
the "aromatic heterocyclic group", or the "condensed polycyclic
aromatic group" included in these groups (R.sub.5 to R.sub.8) via a
linking group such as a substituted or unsubstituted methylene
group, an oxygen atom, a sulfur atom, or a monosubstituted amino
group to form a ring.
[0097] Examples of the "linear or branched alkyl group of 1 to 6
carbon atoms", the "cycloalkyl group of 5 to 10 carbon atoms", or
the "linear or branched alkenyl group of 2 to 6 carbon atoms" in
the "linear or branched alkyl group of 1 to 6 carbon atoms that may
have a substituent", the "cycloalkyl group of 5 to 10 carbon atoms
that may have a substituent", or the "linear or branched alkenyl
group of 2 to 6 carbon atoms that may have a substituent"
represented by R.sub.12 and R.sub.13 in the general formula (7)
include the same groups exemplified as the "linear or branched
alkyl group of 1 to 6 carbon atoms", the "cycloalkyl group of 5 to
10 carbon atoms", or the "linear or branched alkenyl group of 2 to
6 carbon atoms" in the "linear or branched alkyl group of 1 to 6
carbon atoms that may have a substituent", the "cycloalkyl group of
5 to 10 carbon atoms that may have a substituent", or the "linear
or branched alkenyl group of 2 to 6 carbon atoms that may have a
substituent" represented by R.sub.5 to R.sub.11 in the above
general formula (7), and these groups may bind to each other via a
single bond, or a linking group such as a substituted or
unsubstituted methylene group, an oxygen atom, a sulfur atom, or a
monosubstituted amino group to form a ring.
[0098] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "linear or branched alkyl group of 1 to 6
carbon atoms that has a substituent", the "cycloalkyl group of 5 to
10 carbon atoms that has a substituent", or the "linear or branched
alkenyl group of 2 to 6 carbon atoms that has a substituent"
represented by R.sub.5 to R.sub.11 in the above general formula
(7), and possible embodiments may also be the same embodiments as
the exemplified embodiments.
[0099] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by R.sub.12 and R.sub.13 in the general formula
(7) include the same groups exemplified as the "aromatic
hydrocarbon group", the "aromatic heterocyclic group", or the
"condensed polycyclic aromatic group" in the "substituted or
unsubstituted aromatic hydrocarbon group", the "substituted or
unsubstituted aromatic heterocyclic group", or the "substituted or
unsubstituted condensed polycyclic aromatic group" represented by
Ar.sub.1 to Ar.sub.4 in the above general formula (1), and these
groups may bind to each other via a single bond, or a linking group
such as a substituted or unsubstituted methylene group, an oxygen
atom, a sulfur atom, or a monosubstituted amino group to form a
ring.
[0100] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by R.sub.5 to
R.sub.11 in the above general formula (7), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0101] Examples of the "aryloxy group" in the "substituted or
unsubstituted aryloxy group" represented by R.sub.12 and R.sub.13
in the general formula (7) include the same groups exemplified as
the "aryloxy group" in the "substituted or unsubstituted aryloxy
group" represented by R.sub.5 to R.sub.11 in the above general
formula (7), and these groups may bind to each other via a single
bond, or a linking group such as a substituted or unsubstituted
methylene group, an oxygen atom, a sulfur atom, or a
monosubstituted amino group to form a ring.
[0102] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by R.sub.5 to
R.sub.11 in the above general formula (7), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0103] Examples of the "substituent" in the linking group
"monosubstituted amino group" in the general formula (7) include
the same groups exemplified as the "linear or branched alkyl group
of 1 to 6 carbon atoms", the "cycloalkyl group of 5 to 10 carbon
atoms", the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "linear or branched alkyl group of 1 to 6 carbon atoms that
may have a substituent", the "cycloalkyl group of 5 to 10 carbon
atoms that may have a substituent", the "substituted or
unsubstituted aromatic hydrocarbon group", the "substituted or
unsubstituted aromatic heterocyclic group", or the "substituted or
unsubstituted condensed polycyclic aromatic group" represented by
R.sub.5 to R.sub.11 in the above general formula (7).
[0104] Further, these groups may have a substituent, and examples
of the substituent of the "linear or branched alkyl group of 1 to 6
carbon atoms that has a substituent" or the "cycloalkyl group of 5
to 10 carbon atoms that has a substituent" include the same
substituents exemplified as the "substituent" in the "linear or
branched alkyl group of 1 to 6 carbon atoms that has a substituent"
or the "cycloalkyl group of 5 to 10 carbon atoms that has a
substituent" represented by R.sub.5 to R.sub.11 in the above
general formula (7), and examples of the substituent of the
"substituted aromatic hydrocarbon group", the "substituted aromatic
heterocyclic group", or the "substituted condensed polycyclic
aromatic group" include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by R.sub.5 to
R.sub.11 in the above general formula (7), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0105] Ar.sub.1 in the general formula (1) is preferably a
"substituted or unsubstituted aromatic hydrocarbon group" or a
"substituted or unsubstituted condensed polycyclic aromatic group",
more preferably a phenyl group, a biphenylyl group, a terphenylyl
group, a naphthyl group, a phenanthrenyl group, an anthracenyl
group, a fluorenyl group, a carbazolyl group, an indolyl group, a
dibenzofuranyl group, or a dibenzothienyl group.
[0106] Ar.sub.2 in the general formula (1) is preferably a
"substituted or unsubstituted aromatic hydrocarbon group" or a
"substituted or unsubstituted condensed polycyclic aromatic group",
more preferably a phenyl group, a biphenylyl group, a terphenylyl
group, a naphthyl group, a phenanthrenyl group, an anthracenyl
group, or a fluorenyl group, and above all, a phenyl group,
particularly, an unsubstituted phenyl group is preferable.
[0107] As the arylamine compound represented by the general formula
(1), an arylamine compound represented by the following general
formula (1a) or general formula (1b) is more preferably used.
##STR00009##
(In the formula, Ar.sub.1 to Ar.sub.3 represent the same meanings
as described in the above general formula (1), and Ar.sub.16 to
Ar.sub.17 may be the same or different, and represent a substituted
or unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group.)
##STR00010##
(In the formula, Ar.sub.1 to Ar.sub.2 represent the same meanings
as described in the above general formula (1), and Ar.sub.16 to
Ar.sub.19 may be the same or different, and represent a substituted
or unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group.)
[0108] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by Ar.sub.16 to Ar.sub.19 in the general formula
(1a) or the general formula (1b) include the same groups
exemplified as the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by Ar.sub.1 to Ar.sub.4 in the above general
formula (1).
[0109] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments as the exemplified
embodiments.
[0110] In the general formula (1a), Ar.sub.1 and Ar.sub.16 are
preferably the same group, and Ar.sub.2 and Ar.sub.17 are
preferably the same group.
[0111] In the general formula (1b), Ar.sub.1, Ar.sub.16, and
Ar.sub.18 are preferably the same group, and Ar.sub.2, Ar.sub.17,
and Ar.sub.19 are preferably the same group.
[0112] In the general formula (1), the "substituent" in the
"substituted aromatic hydrocarbon group", the "substituted aromatic
heterocyclic group", or the "substituted condensed polycyclic
aromatic group" represented by Ar.sub.1 to Ar.sub.4 is preferably a
deuterium atom, a linear or branched alkyl group of 1 to 6 carbon
atoms that may have a substituent, a linear or branched alkenyl
group of 2 to 6 carbon atoms that may have a substituent, a
"substituted or unsubstituted aromatic hydrocarbon group", or a
"substituted or unsubstituted condensed polycyclic aromatic group",
more preferably a deuterium atom, a phenyl group, a biphenylyl
group, a naphthyl group, or a vinyl group. Further, a case where
these groups bind to each other via a single bond to form a
condensed aromatic ring is also preferable.
[0113] In the hole injection layer of the organic EL device of the
present invention, examples of the electron acceptor doped in the
arylamine compound represented by the above general formula (1)
include trisbromophenylaminehexachloroantimony,
tetracyanoquinodimethane (TCNQ),
2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4TCNQ),
and a radialene derivative (refers to JP-A-2011-100621, for
example), and a radialene derivative represented by the above
general formula (2) is preferably used.
[0114] Ar.sub.5 to Ar.sub.7 in the general formula (2) are
preferably an "aromatic hydrocarbon group", a "condensed polycyclic
aromatic group", or a pyridyl group, more preferably a phenyl
group, a biphenylyl group, a terphenylyl group, a naphthyl group, a
phenanthrenyl group, a fluorenyl group, or a pyridyl group, and the
"electron acceptor group" is preferably a fluorine atom, a chlorine
atom, a cyano group, or a trifluoromethyl group.
[0115] An embodiment in which Ar.sub.5 to Ar.sub.7 in the general
formula (2) are at least partially, preferably completely
substituted with an "electron acceptor group" is preferable.
[0116] Ar.sub.5 to Ar.sub.9 in the general formula (2) are
preferably a phenyl group or a pyridyl group completely substituted
with a fluorine atom, a chlorine atom, a cyano group, or a
trifluoromethyl group such as a tetrafluoropyridyl group, a
tetrafluoro-(trifluoromethyl)phenyl group, a
cyano-tetrafluorophenyl group,
dichloro-difluoro-(trifluoromethyl)phenyl group, or a
pentafluorophenyl group.
[0117] The "aromatic heterocyclic group" in the "substituted or
unsubstituted aromatic heterocyclic group" represented by B.sub.1
in the general formula (3) is preferably a nitrogen-containing
aromatic heterocyclic group such as a pyridyl group, a pyrimidinyl
group, a pyrrolyl group, a quinolyl group, an isoquinolyl group, an
indolyl group, a carbazolyl group, a benzoxazolyl group, a
benzothiazolyl group, a quinoxalinyl group, a benzoimidazolyl
group, a pyrazolyl group, or a carbolinyl group, more preferably a
pyridyl group, a pyrimidinyl group, a quinolyl group, an
isoquinolyl group, an indolyl group, a pyrazolyl group, a
benzoimidazolyl group, or a carbolinyl group.
[0118] p and q in the general formula (3) maintains a relationship
that the sum of p and q (p+q) is 9, and p represents 7 or 8, and q
represents 1 or 2.
[0119] A.sub.1 in the general formula (3) is preferably a "divalent
group of a substituted or unsubstituted aromatic hydrocarbon" or a
"divalent group of a substituted or unsubstituted condensed
polycyclic aromatic", more preferably a divalent group that results
from the removal of two hydrogen atoms from benzene, biphenyl,
naphthalene, or phenanthrene.
[0120] As the compound having an anthracene ring structure
represented by the general formula (3), a compound having an
anthracene ring structure represented by the following general
formula (3a), general formula (3b), or general formula (3c) is more
preferably used.
##STR00011##
(In the formula, A.sub.1 represents the same meaning as described
in the above general formula (3), Ar.sub.20, Ar.sub.21, and
Ar.sub.22 may be the same or different, and represent a substituted
or unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group, R.sub.14 to
R.sub.20 may be the same or different, and represent a hydrogen
atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano
group, a nitro group, a linear or branched alkyl group of 1 to 6
carbon atoms that may have a substituent, a cycloalkyl group of 5
to 10 carbon atoms that may have a substituent, a linear or
branched alkenyl group of 2 to 6 carbon atoms that may have a
substituent, a linear or branched alkyloxy group of 1 to 6 carbon
atoms that may have a substituent, a cycloalkyloxy group of 5 to 10
carbon atoms that may have a substituent, a substituted or
unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, a substituted or
unsubstituted condensed polycyclic aromatic group, or a substituted
or unsubstituted aryloxy group, and may bind to each other via a
single bond, a substituted or unsubstituted methylene group, an
oxygen atom, or a sulfur atom to form a ring, and X.sub.1, X.sub.2,
X.sub.3, and X.sub.4 represent a carbon atom or a nitrogen atom,
and only one of X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is a
nitrogen atom, and the nitrogen atom in this case does not have a
hydrogen atom or a substituent of R.sub.14 to R.sub.17.)
##STR00012##
(In the formula, A.sub.1 represents the same meaning as described
in the above general formula (3), and Ar.sub.23, Ar.sub.24, and
Ar.sub.25 may be the same or different, and represent a substituted
or unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group.)
##STR00013##
(In the formula, A.sub.1 represents the same meaning as described
in the above general formula (3), Ar.sub.26, Ar.sub.27, and
Ar.sub.28 may be the same or different, and represent a substituted
or unsubstituted aromatic hydrocarbon group, a substituted or
unsubstituted aromatic heterocyclic group, or a substituted or
unsubstituted condensed polycyclic aromatic group, R.sub.21
represents a hydrogen atom, a deuterium atom, a fluorine atom, a
chlorine atom, a cyano group, a nitro group, a linear or branched
alkyl group of 1 to 6 carbon atoms that may have a substituent, a
cycloalkyl group of 5 to 10 carbon atoms that may have a
substituent, a linear or branched alkenyl group of 2 to 6 carbon
atoms that may have a substituent, a linear or branched alkyloxy
group of 1 to 6 carbon atoms that may have a substituent, a
cycloalkyloxy group of 5 to 10 carbon atoms that may have a
substituent, a substituted or unsubstituted aromatic hydrocarbon
group, a substituted or unsubstituted aromatic heterocyclic group,
a substituted or unsubstituted condensed polycyclic aromatic group,
or a substituted or unsubstituted aryloxy group.)
[0121] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by Ar.sub.20, Ar.sub.21, and Ar.sub.22 in the
general formula (3a) include the same groups exemplified as the
"aromatic hydrocarbon group", the "aromatic heterocyclic group", or
the "condensed polycyclic aromatic group" in the "substituted or
unsubstituted aromatic hydrocarbon group", the "substituted or
unsubstituted aromatic heterocyclic group", or the "substituted or
unsubstituted condensed polycyclic aromatic group" represented by
Ar.sub.1 to Ar.sub.4 in the above general formula (1).
[0122] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments.
[0123] Specific examples of the "linear or branched alkyl group of
1 to 6 carbon atoms", the "cycloalkyl group of 5 to 10 carbon
atoms", or the "linear or branched alkenyl group of 2 to 6 carbon
atoms" in the "linear or branched alkyl group of 1 to 6 carbon
atoms that may have a substituent", the "cycloalkyl group of 5 to
10 carbon atoms that may have a substituent", or the "linear or
branched alkenyl group of 2 to 6 carbon atoms that may have a
substituent" represented by R.sub.14 to R.sub.20 in the general
formula (3a) include a methyl group, an ethyl group, an n-propyl
group, an isopropyl group, an n-butyl group, an isobutyl group, a
tert-butyl group, an n-pentyl group, an isopentyl group, a
neopentyl group, an n-hexyl group, a cyclopentyl group, a
cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a vinyl
group, an allyl group, an isopropenyl group, and a 2-butenyl group,
and these groups may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring.
[0124] Specific examples of the "substituent" in the "linear or
branched alkyl group of 1 to 6 carbon atoms that has a
substituent", the "cycloalkyl group of 5 to 10 carbon atoms that
has a substituent", or the "linear or branched alkenyl group of 2
to 6 carbon atoms that has a substituent" represented by R.sub.14
to R.sub.20 in the general formula (3a) include a deuterium atom, a
cyano group, a nitro group; halogen atoms such as a fluorine atom,
a chlorine atom, a bromine atom, and an iodine atom; linear or
branched alkyloxy groups of 1 to 6 carbon atoms such as a methyloxy
group, an ethyloxy group, and a propyloxy group; alkenyl groups
such as a vinyl group and an allyl group; aryloxy groups such as a
phenyloxy group and a tolyloxy group; arylalkyloxy groups such as a
benzyloxy group and a phenethyloxy group; aromatic hydrocarbon
groups or condensed polycyclic aromatic groups such as a phenyl
group, a biphenylyl group, a terphenylyl group, a naphthyl group,
an anthracenyl group, a phenanthrenyl group, a fluorenyl group, an
indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl
group, and a triphenylenyl group; aromatic heterocyclic groups such
as a pyridyl group, a pyrimidinyl group, a triazinyl group, a
thienyl group, a furyl group, a pyrrolyl group, a quinolyl group,
an isoquinolyl group, a benzofuranyl group, a benzothienyl group,
an indolyl group, a carbazolyl group, a benzoxazolyl group, a
benzothiazolyl group, a quinoxalinyl group, a benzoimidazolyl
group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl
group, and a carbolinyl group; and other groups, and these
substituents may be further substituted with a substituent
exemplified above. Further, these substituents may bind to each
other via a single bond, a substituted or unsubstituted methylene
group, an oxygen atom, or a sulfur atom to form a ring.
[0125] Specific examples of the "linear or branched alkyloxy group
of 1 to 6 carbon atoms" or the "cycloalkyloxy group of 5 to 10
carbon atoms" in the "linear or branched alkyloxy group of 1 to 6
carbon atoms that may have a substituent" or the "cycloalkyloxy
group of 5 to 10 carbon atoms that may have a substituent"
represented by R.sub.14 to R.sub.20 in the general formula (3a)
include a methyloxy group, an ethyloxy group, an n-propyloxy group,
an isopropyloxy group, an n-butyloxy group, a tert-butyloxy group,
an n-pentyloxy group, an n-hexyloxy group, a cyclopentyloxy group,
a cyclohexyloxy group, a cycloheptyloxy group, a cyclooctyloxy
group, a 1-adamantyloxy group, and a 2-adamantyloxy group, and
these groups may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring.
[0126] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "linear or branched alkyl group of 1 to 6
carbon atoms that has a substituent", the "cycloalkyl group of 5 to
10 carbon atoms that has a substituent", or the "linear or branched
alkenyl group of 2 to 6 carbon atoms that has a substituent"
represented by R.sub.14 to R.sub.20 in the above general formula
(3a), and possible embodiments may also be the same embodiments as
the exemplified embodiments.
[0127] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by R.sub.14 to R.sub.20 in the general formula
(3a) include the same groups exemplified as the "aromatic
hydrocarbon group", the "aromatic heterocyclic group", or the
"condensed polycyclic aromatic group" in the "substituted or
unsubstituted aromatic hydrocarbon group", the "substituted or
unsubstituted aromatic heterocyclic group", or the "substituted or
unsubstituted condensed polycyclic aromatic group" represented by
Ar.sub.1 to Ar.sub.4 in the above general formula (1), and these
groups may bind to each other via a single bond, a substituted or
unsubstituted methylene group, an oxygen atom, or a sulfur atom to
form a ring.
[0128] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments.
[0129] Specific examples of the "aryloxy group" in the "substituted
or unsubstituted aryloxy group" represented by R.sub.14 to R.sub.20
in the general formula (3a) include a phenyloxy group, a
biphenylyloxy group, a terphenylyloxy group, a naphthyloxy group,
an anthracenyloxy group, a phenanthrenyloxy group, a fluorenyloxy
group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy
group, and these groups may bind to each other via a single bond, a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring.
[0130] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments.
[0131] In the general formula (3a), X.sub.1, X.sub.2, X.sub.3, and
X.sub.4 represent a carbon atom or a nitrogen atom, and only one of
X.sub.1, X.sub.2, X.sub.3, and X.sub.4 is a nitrogen atom (the rest
are each a carbon atom), and the nitrogen atom in this case does
not have a hydrogen atom or a substituent of R.sub.14 to R.sub.17.
That is, it means that in the case where X.sub.1 is a nitrogen
atom, R.sub.14, in the case where X.sub.2 is a nitrogen atom,
R.sub.15, in the case where X.sub.3 is a nitrogen atom, R.sub.16,
and in the case where X.sub.4 is a nitrogen atom, R.sub.17 is not
present.
[0132] In the general formula (3a), X.sub.3 is preferably a
nitrogen atom (X.sub.1, X.sub.2, and X.sub.4 are each a carbon
atom), and in this case, a hydrogen atom or a substituent of
R.sub.16 is not present.
[0133] Further, as for the bonding position of the linking group
L.sub.1, L.sub.1 preferably binds at a position corresponding to
the para position of the nitrogen atom of a pyridoindole ring.
[0134] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by Ar.sub.23, Ar.sub.24, and Ar.sub.25 in the
general formula (3b) include the same groups exemplified as the
"aromatic hydrocarbon group", the "aromatic heterocyclic group", or
the "condensed polycyclic aromatic group" in the "substituted or
unsubstituted aromatic hydrocarbon group", the "substituted or
unsubstituted aromatic heterocyclic group", or the "substituted or
unsubstituted condensed polycyclic aromatic group" represented by
Ar.sub.1 to Ar.sub.4 in the above general formula (1).
[0135] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments.
[0136] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by Ar.sub.26, Ar.sub.27, and Ar.sub.28 in the
general formula (3c) include the same groups exemplified as the
"aromatic hydrocarbon group", the "aromatic heterocyclic group", or
the "condensed polycyclic aromatic group" in the "substituted or
unsubstituted aromatic hydrocarbon group", the "substituted or
unsubstituted aromatic heterocyclic group", or the "substituted or
unsubstituted condensed polycyclic aromatic group" represented by
Ar.sub.1 to Ar.sub.4 in the above general formula (1).
[0137] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments.
[0138] Examples of the "linear or branched alkyl group of 1 to 6
carbon atoms", the "cycloalkyl group of 5 to 10 carbon atoms", or
the "linear or branched alkenyl group of 2 to 6 carbon atoms" in
the "linear or branched alkyl group of 1 to 6 carbon atoms that may
have a substituent", the "cycloalkyl group of 5 to 10 carbon atoms
that may have a substituent", or the "linear or branched alkenyl
group of 2 to 6 carbon atoms that may have a substituent"
represented by R.sub.21 in the general formula (3c) include the
same groups exemplified as the "linear or branched alkyl group of 1
to 6 carbon atoms", the "cycloalkyl group of 5 to 10 carbon atoms",
or the "linear or branched alkenyl group of 2 to 6 carbon atoms" in
the "linear or branched alkyl group of 1 to 6 carbon atoms that may
have a substituent", the "cycloalkyl group of 5 to 10 carbon atoms
that may have a substituent", or the "linear or branched alkenyl
group of 2 to 6 carbon atoms that may have a substituent"
represented by R.sub.14 to R.sub.20 in the above general formula
(3a).
[0139] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "linear or branched alkyl group of 1 to 6
carbon atoms that has a substituent", the "cycloalkyl group of 5 to
10 carbon atoms that has a substituent", or the "linear or branched
alkenyl group of 2 to 6 carbon atoms that has a substituent"
represented by R.sub.14 to R.sub.20 in the above general formula
(3a), and possible embodiments may also be the same embodiments as
the exemplified embodiments.
[0140] Examples of the "linear or branched alkyloxy group of 1 to 6
carbon atoms" or the "cycloalkyloxy group of 5 to 10 carbon atoms"
in the "linear or branched alkyloxy group of 1 to 6 carbon atoms
that may have a substituent" or the "cycloalkyloxy group of 5 to 10
carbon atoms that may have a substituent" represented by R.sub.21
in the general formula (3c) include the same groups exemplified as
the "linear or branched alkyloxy group of 1 to 6 carbon atoms" or
the "cycloalkyloxy group of 5 to 10 carbon atoms" in the "linear or
branched alkyloxy group of 1 to 6 carbon atoms that may have a
substituent" or the "cycloalkyloxy group of 5 to 10 carbon atoms
that may have a substituent" represented by R.sub.14 to R.sub.20 in
the above general formula (3a).
[0141] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "linear or branched alkyl group of 1 to 6
carbon atoms that has a substituent", the "cycloalkyl group of 5 to
10 carbon atoms that has a substituent", or the "linear or branched
alkenyl group of 2 to 6 carbon atoms that has a substituent"
represented by R.sub.14 to R.sub.20 in the above general formula
(3a), and possible embodiments may also be the same embodiments as
the exemplified embodiments.
[0142] Examples of the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in the "substituted or unsubstituted aromatic hydrocarbon group",
the "substituted or unsubstituted aromatic heterocyclic group", or
the "substituted or unsubstituted condensed polycyclic aromatic
group" represented by R.sub.21 in the general formula (3c) include
the same groups exemplified as the "aromatic hydrocarbon group",
the "aromatic heterocyclic group", or the "condensed polycyclic
aromatic group" in the "substituted or unsubstituted aromatic
hydrocarbon group", the "substituted or unsubstituted aromatic
heterocyclic group", or the "substituted or unsubstituted condensed
polycyclic aromatic group" represented by Ar.sub.1 to Ar.sub.4 in
the above general formula (1).
[0143] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments.
[0144] Examples of the "aryloxy group" in the "substituted or
unsubstituted aryloxy group" represented by R.sub.21 in the general
formula (3c) include the same groups exemplified as the "aryloxy
group" in the "substituted or unsubstituted aryloxy group"
represented by R.sub.14 to R.sub.20 in the above general formula
(3a).
[0145] Further, these groups may have a substituent, and examples
of the substituent include the same substituents exemplified as the
"substituent" in the "substituted aromatic hydrocarbon group", the
"substituted aromatic heterocyclic group", or the "substituted
condensed polycyclic aromatic group" represented by Ar.sub.1 to
Ar.sub.4 in the above general formula (1), and possible embodiments
may also be the same embodiments.
[0146] Ar.sub.8 in the general formula (4) is preferably a phenyl
group, a biphenylyl group, a naphthyl group, an anthracenyl group,
an acenaphthenyl group, a phenanthrenyl group, a fluorenyl group,
an indenyl group, a pyrenyl group, a perylenyl group, a
fluoranthenyl group, or a triphenylenyl group, more preferably a
phenyl group, a biphenylyl group, a naphthyl group, an anthracenyl
group, a phenanthrenyl group, a pyrenyl group, a fluoranthenyl
group, or a triphenylenyl group. Here, the phenyl group preferably
has a substituted or unsubstituted condensed polycyclic aromatic
group as a substituent, more preferably has a substituent selected
from a naphthyl group, an anthracenyl group, a phenanthrenyl group,
a pyrenyl group, a fluoranthenyl group, or a triphenylenyl
group.
[0147] Ar.sub.9 in the general formula (4) is preferably a phenyl
group that has a substituent, and the substituent in this case is
preferably an aromatic hydrocarbon group such as a phenyl group, a
biphenylyl group, or a terphenylyl group, or a condensed polycyclic
aromatic group such as a naphthyl group, an anthracenyl group, an
acenaphthenyl group, a phenanthrenyl group, a fluorenyl group, an
indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl
group, or a triphenylenyl group, more preferably a phenyl group, a
naphthyl group, an anthracenyl group, a phenanthrenyl group, a
pyrenyl group, a fluoranthenyl group, or a triphenylenyl group.
[0148] Ar.sub.10 in the general formula (4) is preferably a phenyl
group that has a substituent, and the substituent in this case is
preferably an aromatic hydrocarbon group such as a phenyl group, a
biphenylyl group, or a terphenylyl group, or a condensed polycyclic
aromatic group such as a naphthyl group, an anthracenyl group, an
acenaphthenyl group, a phenanthrenyl group, a fluorenyl group, an
indenyl group, a pyrenyl group, a perylenyl group, a fluoranthenyl
group, or a triphenylenyl group, more preferably a phenyl group, a
naphthyl group, an anthracenyl group, a phenanthrenyl group, a
pyrenyl group, a fluoranthenyl group, or a triphenylenyl group.
[0149] It is preferable that in the general formula (4), Ar.sub.8
and Ar.sub.9 are not the same from the viewpoint of stability as a
thin film. Here, when Ar.sub.8 and Ar.sub.9 are the same group,
they may have a different substituent or the substitution position
may be different.
[0150] In the general formula (4), Ar.sub.9 and Ar.sub.10 may be
the same group, however, there is a risk that crystallization is
likely to occur due to an increase in symmetry of the molecule as a
whole, and from the viewpoint of stability as a thin film, Ar.sub.9
and Ar.sub.10 are preferably different groups, and Ar.sub.9 and
Ar.sub.10 are not simultaneously a hydrogen atom.
[0151] Further, it is preferable that one of Ar.sub.9 and Ar.sub.10
is a hydrogen atom.
[0152] Example of the compound having a pyrimidine ring structure
represented by the general formula (4) include compounds having a
pyrimidine ring structure represented by the following general
formula (4a) and general formula (4b) in which a bonding pattern of
a substituent is different.
##STR00014##
(In the formula, Ar.sub.8, Ar.sub.9, Ar.sub.10, and E represent the
same meanings as described in the above general formula (4).)
##STR00015##
(In the formula, Ar.sub.8, Ar.sub.9, Ar.sub.10, and E represent the
same meanings as described in the above general formula (4).)
[0153] Ar.sub.11 in the structural formula (5) is preferably a
nitrogen-containing heterocyclic group such as a triazinyl group, a
pyridyl group, a pyrimidinyl group, a pyrrolyl group, a quinolyl
group, an isoquinolyl group, an indolyl group, a carbazolyl group,
a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group,
a benzoimidazolyl group, a pyrazolyl group, a naphthyridinyl group,
a phenanthrolinyl group, an acridinyl group, or a carbolinyl group,
more preferably a triazinyl group, a pyridyl group, a pyrimidinyl
group, a quinolyl group, an isoquinolyl group, an indolyl group, a
quinoxalinyl group, a benzoimidazolyl group, a naphthyridinyl
group, a phenanthrolinyl group, or an acridinyl group, particularly
preferably a pyridyl group, a pyrimidinyl group, a quinolyl group,
an isoquinolyl group, an indolyl group, a quinoxalinyl group, a
benzoimidazolyl group, a phenanthrolinyl group, or an acridinyl
group.
[0154] In the structural formula (5), a bonding position of
Ar.sub.11 in the benzene ring is preferably a meta position with
respect to a bonding position of the pyrimidine ring shown in the
general formula (4) as shown in the following structural formula
(5a) from the viewpoint of stability as a thin film.
##STR00016##
(In the formula, Ar.sub.11, and R.sub.1 to R.sub.4 represent the
same meanings as described in the above structural formula
(5).)
[0155] Ar.sub.12 and Ar.sub.13 in the general formula (6) are
preferably a "substituted or unsubstituted aromatic hydrocarbon
group", a "substituted or unsubstituted condensed polycyclic
aromatic group", or a pyridyl group, a dibenzothienyl group, a
carbazolyl group, or a dibenzofuranyl group, more preferably a
phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl
group, an anthracenyl group, a phenanthrenyl group, a fluorenyl
group, an indenyl group, a pyrenyl group, a pyridyl group, a
carbazolyl group, or a dibenzofuranyl group, particularly
preferably a phenyl group, a biphenylyl group, a terphenylyl group,
a naphthyl group, an anthracenyl group, a phenanthrenyl group, or a
fluorenyl group.
[0156] Then, the substituent that these groups may have is
preferably an "aromatic hydrocarbon group", an "aromatic
heterocyclic group", or a "condensed polycyclic aromatic group"
such as a phenyl group, a biphenylyl group, a terphenylyl group, a
tetrakisphenyl group, a styryl group, a naphthyl group, an
anthracenyl group, an acenaphthenyl group, a phenanthrenyl group, a
fluorenyl group, an indenyl group, a pyrenyl group, a pyridyl
group, a triazinyl group, a pyrimidinyl group, a furyl group, a
pyrrolyl group, a thienyl group, a quinolyl group, an isoquinolyl
group, a benzofuranyl group, a benzothienyl group, an indolyl
group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl
group, a quinoxalinyl group, a benzoimidazolyl group, a pyrazolyl
group, a dibenzofuranyl group, a dibenzothienyl group, a
naphthyridinyl group, a phenanthrolinyl group, or an acridinyl
group, more preferably a phenyl group, a biphenylyl group, a
naphthyl group, an anthracenyl group, a phenanthrenyl group, a
fluorenyl group, a pyrenyl group, a pyridyl group, a triazinyl
group, a pyrimidinyl group, a quinolyl group, an isoquinolyl group,
an indolyl group, a carbazolyl group, a quinoxalinyl group, a
benzoimidazolyl group, a pyrazolyl group, a phenanthrolinyl group,
or an acridinyl group, particularly preferably a phenyl group, a
naphthyl group, an anthracenyl group, a pyridyl group, a quinolyl
group, or an isoquinolyl group.
[0157] L.sub.1 in the general formula (6) is preferably a "divalent
group of a substituted or unsubstituted aromatic hydrocarbon", a
"divalent group of a substituted or unsubstituted condensed
polycyclic aromatic", or a pyridylene group or a bipyridylene
group, more preferably a divalent group derived from benzene,
biphenyl, naphthalene, anthracene, fluorene, phenanthrene, pyrene,
or pyridine, particularly preferably a divalent group derived from
benzene, naphthalene, or pyridine.
[0158] L.sub.2 in the general formula (6) is preferably a single
bond, or a divalent group derived from naphthalene, anthracene,
fluorene, phenanthrene, or pyrene, more preferably a single bond,
or a divalent group derived from naphthalene or anthracene.
[0159] B.sub.2 in the general formula (6) is preferably a
nitrogen-containing aromatic heterocyclic group such as a pyridyl
group, a bipyridyl group, a triazinyl group, a pyrimidinyl group, a
pyrrolyl group, a quinolyl group, an isoquinolyl group, an indolyl
group, a carbazolyl group, a carbolinyl group, a benzoxazolyl
group, a benzothiazolyl group, a quinoxalinyl group, a
benzoimidazolyl group, a pyrazolyl group, a naphthyridinyl group, a
phenanthrolinyl group, or an acridinyl group, more preferably a
pyridyl group, a bipyridyl group, a pyrimidinyl group, a quinolyl
group, an isoquinolyl group, an indolyl group, a carbolinyl group,
a quinoxalinyl group, a benzoimidazolyl group, a naphthyridinyl
group, or a phenanthrolinyl group, particularly preferably a
pyridyl group, a quinolyl group, or an isoquinolyl group.
[0160] In the general formula (6), when L.sub.1 is a divalent group
that results from the removal of two hydrogen atoms from
substituted or unsubstituted benzene and L.sub.2 is a single bond,
B.sub.2 is preferably a nitrogen-containing aromatic heterocyclic
group having a condensed polycyclic structure such as a pyridyl
group, a bipyridyl group, a quinolyl group, an isoquinolyl group,
an indolyl group, a carbazolyl group, a carbolinyl group, a
benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a
benzoimidazolyl group, a naphthyridinyl group, a phenanthrolinyl
group, or an acridinyl group, more preferably a pyridyl group, a
bipyridyl group, a quinolyl group, an isoquinolyl group, an indolyl
group, a carbolinyl group, a quinoxalinyl group, a benzoimidazolyl
group, a naphthyridinyl group, or a phenanthrolinyl group,
particularly preferably a pyridyl group, a bipyridyl group, a
quinolyl group, or an isoquinolyl group.
[0161] In the general formula (6), when B.sub.2 is a pyridyl group
or a bipyridyl group and L.sub.2 is a single bond, L.sub.1 is more
preferably a divalent group that results from the removal of two
hydrogen atoms from benzene, biphenyl, naphthalene, anthracene,
fluorene, phenanthrene, or pyrene, or a single bond, particularly
preferably a divalent group that results from the removal of two
hydrogen atoms from benzene or biphenyl, or a single bond.
[0162] A.sub.2 in the general formula (7) is preferably a "divalent
group of a substituted or unsubstituted aromatic hydrocarbon" or a
single bond, more preferably a divalent group that results from the
removal of two hydrogen atoms from benzene, biphenyl, or
naphthalene, or a single bond, particularly preferably a single
bond.
[0163] Ar.sub.14 and Ar.sub.15 in the general formula (7) are
preferably a phenyl group, a biphenylyl group, a naphthyl group, a
fluorenyl group, an indenyl group, a pyridyl group, a
dibenzofuranyl group, or a pyridobenzofuranyl group.
[0164] Ar.sub.14 and Ar.sub.15 in the general formula (7) may bind
to each other directly or through substituents included in these
groups via a single bond, a substituted or unsubstituted methylene
group, an oxygen atom, or a sulfur atom to form a ring.
[0165] It is preferable that at least one of R.sub.5 to R.sub.8 in
the general formula (7) is a "disubstituted amino group substituted
with a group selected from an aromatic hydrocarbon group, an
aromatic heterocyclic group, or a condensed polycyclic aromatic
group", and the "aromatic hydrocarbon group", the "aromatic
heterocyclic group", or the "condensed polycyclic aromatic group"
in this case is preferably a phenyl group, a biphenylyl group, a
naphthyl group, a fluorenyl group, an indenyl group, a pyridyl
group, a dibenzofuranyl group, or a pyridobenzofuranyl group.
[0166] An embodiment in which adjacent two or all of R.sub.5 to
R.sub.8 in the general formula (7) are a vinyl group and adjacent
two vinyl groups bind to each other via a single bond to form a
condensed ring, that is, an embodiment in which a naphthalene ring
or a phenanthrene ring is formed along with the benzene ring to
which R.sub.5 to R.sub.8 bind is also preferable.
[0167] An embodiment in which in the general formula (7), one of
R.sub.5 to R.sub.8 is an "aromatic hydrocarbon group" and binds to
the benzene ring to which R.sub.5 to R.sub.8 bind via a substituted
or unsubstituted methylene group, an oxygen atom, or a sulfur atom
to form a ring is preferable. An embodiment in which the "aromatic
hydrocarbon group" in this case is a phenyl group and binds to the
benzene ring to which R.sub.5 to R.sub.8 bind via an oxygen atom or
a sulfur atom to form a ring, that is, an embodiment in which a
dibenzofuran ring or a dibenzothiophene ring is formed along with
the benzene ring to which R.sub.5 to R.sub.8 bind is particularly
preferable.
[0168] An embodiment in which in the general formula (7), one of
R.sub.9 to R.sub.11 is an "aromatic hydrocarbon group" and binds to
the benzene ring to which R.sub.9 to R.sub.11 bind via a
substituted or unsubstituted methylene group, an oxygen atom, or a
sulfur atom to form a ring is preferable. An embodiment in which
the "aromatic hydrocarbon group" in this case is a phenyl group and
binds to the benzene ring to which R.sub.9 to R.sub.11 bind via an
oxygen atom or a sulfur atom to form a ring, that is, an embodiment
in which a dibenzofuran ring or a dibenzothiophene ring is formed
is particularly preferable.
[0169] As described above, in the amine derivatives having a
condensed ring structure represented by the general formula (7), as
the embodiment in which these groups represented by R.sub.5 to
R.sub.11 bind to each other to form a ring, or the embodiment in
which R.sub.5 to R.sub.11 bind to the benzene ring to which R.sub.5
to R.sub.11 bind to form a ring, an embodiment represented by the
following general formula (7a-a), (7a-b), (7b-a), (7b-b), (7b-c),
(7b-d), (7c-a), or (7c-b) is preferably used.
##STR00017## ##STR00018##
(In the formula, X and Y may be the same or different, and
represent an oxygen atom or a sulfur atom, A.sub.2, Ar.sub.14,
Ar.sub.15, R.sub.5 to R.sub.8, R.sub.11, and R.sub.12 to R.sub.13
represent the same meanings as described in the above general
formula (7).)
[0170] R.sub.12 and R.sub.13 in the general formula (7) are
preferably a "substituted or unsubstituted aromatic hydrocarbon
group", a "substituted or unsubstituted oxygen-containing aromatic
heterocyclic group", or a "substituted or unsubstituted condensed
polycyclic aromatic group", more preferably a phenyl group, a
naphthyl group, a phenanthrenyl group, a pyridyl group, a quinolyl
group, an isoquinolyl group, or a dibenzofuranyl group,
particularly preferably a phenyl group.
[0171] Then, an embodiment in which R.sub.12 and R.sub.13 bind to
each other via a single bond, or a linking group such as a
substituted or unsubstituted methylene group, an oxygen atom, a
sulfur atom, or a monosubstituted amino group to form a ring is
preferable, and an embodiment in which R.sub.12 and R.sub.13 bind
to each other via a single bond is particularly preferable.
[0172] As described above, in the amine derivatives having a
condensed ring structure represented by the general formula (7), as
the embodiment in which R.sub.12 and R.sub.13 bind to each other to
form a ring, an embodiment represented by the following general
formula (7a-a1), (7a-b1), (7b-a1), (7b-b1), (7b-c1), (7b-d1),
(7c-a1), or (7c-b1) is preferably used.
##STR00019## ##STR00020##
(In the formula, X and Y may be the same or different, and
represent an oxygen atom or a sulfur atom, and A.sub.2, Ar.sub.14,
Ar.sub.15, R.sub.5 to R.sub.8, and R.sub.11 represent the same
meanings as described in the above general formula (7).)
[0173] The arylamine compounds of the general formula (1), for
preferred use in the organic EL device of the present invention,
can be used as a constitutive material of a hole injection layer or
a hole transport layer of an organic EL device. The arylamine
compounds of the general formula (1) have high hole mobility and
are therefore preferred compounds as material of a hole injection
layer or a hole transport layer.
[0174] The radialene derivatives of the general formula (2) for
preferred use in the organic EL device of the present invention are
preferred compounds as a p-doping material into a material commonly
used for a hole injection layer or a hole transport layer of an
organic EL device.
[0175] The compounds of the general formula (3) having an
anthracene ring structure, for preferable use in the organic EL
device of the present invention, are preferred compounds as a
constitutive material of an electron transport layer of an organic
EL device.
[0176] The compounds of the general formula (4) having a pyrimidine
ring structure, for preferable use in the organic EL device of the
present invention, are preferred compounds as a constitutive
material of an electron transport layer of an organic EL
device.
[0177] The compounds of the general formula (6) having a
benzotriazole ring structure, for preferable use in the organic EL
device of the present invention, are preferred compounds as a
constitutive material of an electron transport layer of an organic
EL device.
[0178] The amine derivatives of the general formula (7) having a
condensed ring structure, for preferred use in the organic EL
device of the present invention, can be used as a constitutive
material of a light emitting layer of an organic EL device. The
amine derivatives of the general formula (2) having a condensed
ring structure excel in luminous efficiency compared with
conventional materials and are therefore preferred compounds as
dopant material of a light emitting layer.
[0179] In the organic EL device of the present invention, materials
for an organic EL device having excellent hole injection and
transport performances, stability as a thin film, and durability
are combined while taking carrier balance into consideration, and
therefore, compared with the conventional organic EL devices, hole
transport efficiency to the hole transport layer from the anode is
improved (and further, a specific arylamine compound (having a
specific structure) is used in the hole transport layer), and as a
result, luminous efficiency is improved and also durability of the
organic EL device can be improved while maintaining low driving
voltage.
[0180] Thus, an organic EL device having low driving voltage, high
luminous efficiency, and a long lifetime can be attained.
Effects of the Invention
[0181] The organic EL device of the present invention can achieve
an organic EL device having excellent hole injection and transport
performances, low driving voltage, and high luminous efficiency by
selecting a specific arylamine compound (having a specific
structure) capable of effectively exhibiting hole injection and
transport roles as a material of a hole injection layer and
p-doping the compound with an electron acceptor so that holes can
be efficiently injected and transported into a hole transport layer
from an electrode, and thus, hole injection and transport
efficiency into a light emitting layer can be improved.
[0182] Further, an organic EL device having low driving voltage,
high luminous efficiency, and a long lifetime can be realized by
selecting a specific arylamine compound (having a specific
structure) without p-doping as a material of the hole transport
layer, and combining the compound so that carrier balance can be
refined.
[0183] According to the present invention, luminous efficiency,
particularly durability can be improved while maintaining low
driving voltage of the conventional organic EL device.
BRIEF DESCRIPTION OF THE DRAWINGS
[0184] FIG. 1 is a diagram illustrating the configuration of the
organic EL devices of Examples 61 and 72 and Comparative Examples 1
to 8.
MODE FOR CARRYING OUT THE INVENTION
[0185] The following presents specific examples of preferred
compounds among the arylamine compounds of the general formula (1)
preferably used in the organic EL device of the present invention.
The present invention, however, is not restricted to these
compounds.
##STR00021## ##STR00022## ##STR00023## ##STR00024## ##STR00025##
##STR00026## ##STR00027## ##STR00028## ##STR00029## ##STR00030##
##STR00031## ##STR00032## ##STR00033## ##STR00034## ##STR00035##
##STR00036## ##STR00037## ##STR00038## ##STR00039## ##STR00040##
##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045##
##STR00046## ##STR00047## ##STR00048## ##STR00049## ##STR00050##
##STR00051## ##STR00052## ##STR00053## ##STR00054## ##STR00055##
##STR00056## ##STR00057## ##STR00058## ##STR00059## ##STR00060##
##STR00061## ##STR00062## ##STR00063## ##STR00064## ##STR00065##
##STR00066## ##STR00067## ##STR00068## ##STR00069## ##STR00070##
##STR00071## ##STR00072## ##STR00073## ##STR00074## ##STR00075##
##STR00076## ##STR00077## ##STR00078## ##STR00079## ##STR00080##
##STR00081## ##STR00082## ##STR00083## ##STR00084## ##STR00085##
##STR00086## ##STR00087## ##STR00088## ##STR00089## ##STR00090##
##STR00091## ##STR00092## ##STR00093## ##STR00094##
[0186] The arylamine compounds described above can be synthesized
by a known method (refer to Patent Document 7, for example).
[0187] The following presents specific examples of preferred
compounds among the compounds of the general formula (3a)
preferably used in the organic EL device of the present invention
and having an anthracene ring structure. The present invention,
however, is not restricted to these compounds.
##STR00095## ##STR00096## ##STR00097## ##STR00098## ##STR00099##
##STR00100## ##STR00101##
[0188] The following presents specific examples of preferred
compounds among the compounds of the general formula (3b)
preferably used in the organic EL device of the present invention
and having an anthracene ring structure. The present invention,
however, is not restricted to these compounds.
##STR00102## ##STR00103## ##STR00104## ##STR00105## ##STR00106##
##STR00107##
[0189] The following presents specific examples of preferred
compounds among the compounds of the general formula (3c)
preferably used in the organic EL device of the present invention
and having an anthracene ring structure. The present invention,
however, is not restricted to these compounds.
##STR00108## ##STR00109## ##STR00110## ##STR00111## ##STR00112##
##STR00113## ##STR00114## ##STR00115## ##STR00116## ##STR00117##
##STR00118## ##STR00119## ##STR00120## ##STR00121##
##STR00122##
[0190] The compounds having an anthracene ring structure described
above can be synthesized by a known method (refer to Patent
Documents 8 to 10, for example).
[0191] The following presents specific examples of preferred
compounds among the compounds of the general formula (4) preferably
used in the organic EL device of the present invention and having a
pyrimidine ring structure. The present invention, however, is not
restricted to these compounds.
##STR00123## ##STR00124## ##STR00125## ##STR00126## ##STR00127##
##STR00128## ##STR00129## ##STR00130## ##STR00131## ##STR00132##
##STR00133## ##STR00134## ##STR00135## ##STR00136## ##STR00137##
##STR00138## ##STR00139## ##STR00140## ##STR00141## ##STR00142##
##STR00143## ##STR00144## ##STR00145## ##STR00146## ##STR00147##
##STR00148## ##STR00149## ##STR00150## ##STR00151## ##STR00152##
##STR00153## ##STR00154## ##STR00155## ##STR00156## ##STR00157##
##STR00158## ##STR00159## ##STR00160## ##STR00161## ##STR00162##
##STR00163## ##STR00164## ##STR00165## ##STR00166## ##STR00167##
##STR00168## ##STR00169## ##STR00170## ##STR00171## ##STR00172##
##STR00173## ##STR00174## ##STR00175## ##STR00176## ##STR00177##
##STR00178## ##STR00179## ##STR00180## ##STR00181## ##STR00182##
##STR00183## ##STR00184## ##STR00185## ##STR00186## ##STR00187##
##STR00188## ##STR00189## ##STR00190## ##STR00191## ##STR00192##
##STR00193## ##STR00194## ##STR00195## ##STR00196## ##STR00197##
##STR00198## ##STR00199## ##STR00200## ##STR00201## ##STR00202##
##STR00203## ##STR00204## ##STR00205## ##STR00206## ##STR00207##
##STR00208## ##STR00209## ##STR00210## ##STR00211## ##STR00212##
##STR00213## ##STR00214## ##STR00215## ##STR00216## ##STR00217##
##STR00218## ##STR00219## ##STR00220## ##STR00221## ##STR00222##
##STR00223## ##STR00224## ##STR00225## ##STR00226## ##STR00227##
##STR00228## ##STR00229## ##STR00230## ##STR00231## ##STR00232##
##STR00233## ##STR00234## ##STR00235## ##STR00236##
##STR00237##
[0192] The compounds having a pyrimidine ring structure described
above can be synthesized by a known method (refer to Patent
Documents 8 and 9, for example).
[0193] The following presents specific examples of preferred
compounds among the compounds of the general formula (6) preferably
used in the organic EL device of the present invention and having a
benzotriazole ring structure. The present invention, however, is
not restricted to these compounds.
##STR00238## ##STR00239## ##STR00240## ##STR00241## ##STR00242##
##STR00243## ##STR00244## ##STR00245## ##STR00246## ##STR00247##
##STR00248## ##STR00249## ##STR00250## ##STR00251## ##STR00252##
##STR00253## ##STR00254## ##STR00255## ##STR00256## ##STR00257##
##STR00258## ##STR00259## ##STR00260## ##STR00261## ##STR00262##
##STR00263## ##STR00264## ##STR00265## ##STR00266## ##STR00267##
##STR00268## ##STR00269## ##STR00270## ##STR00271## ##STR00272##
##STR00273## ##STR00274## ##STR00275## ##STR00276## ##STR00277##
##STR00278## ##STR00279## ##STR00280## ##STR00281## ##STR00282##
##STR00283## ##STR00284## ##STR00285##
[0194] The compounds having a benzotriazole ring structure
described above can be synthesized by a known method (refer to
Patent Document 11, for example).
[0195] The following presents specific examples of preferred
compounds among the amine derivatives of the general formula (7)
preferably used in the organic EL device of the present invention
and having a condensed ring structure. The present invention,
however, is not restricted to these compounds.
##STR00286## ##STR00287## ##STR00288## ##STR00289## ##STR00290##
##STR00291## ##STR00292## ##STR00293## ##STR00294##
[0196] The arylamine compounds of the general formula (1) were
purified by methods such as column chromatography, adsorption
using, for example, a silica gel, activated carbon, or activated
clay, recrystallization or crystallization using a solvent, and a
sublimation purification method. The compounds were identified by
an NMR analysis. A melting point, a glass transition point (Tg),
and a work function were measured as material property values. The
melting point can be used as an index of vapor deposition, the
glass transition point (Tg) as an index of stability in a thin-film
state, and the work function as an index of hole transportability
and hole blocking performance.
[0197] Other compounds used for the organic EL device of the
present invention were purified by methods such as column
chromatography, adsorption using, for example, a silica gel,
activated carbon, or activated clay, and recrystallization or
crystallization using a solvent, and finally purified by
sublimation.
[0198] The melting point and the glass transition point (Tg) were
measured by a high-sensitive differential scanning calorimeter
(DSC3100SA produced by Bruker AXS) using powder.
[0199] For the measurement of the work function, a 100 nm-thick
thin film was fabricated on an ITO substrate, and an ionization
potential measuring device (PYS-202 produced by Sumitomo Heavy
Industries, Ltd.) was used.
[0200] The organic EL device of the present invention may have a
structure including an anode, a hole injection layer, a hole
transport layer, a light emitting layer, an electron transport
layer, an electron injection layer, and a cathode successively
formed on a substrate, optionally with an electron blocking layer
between the hole transport layer and the light emitting layer, and
a hole blocking layer between the light emitting layer and the
electron transport layer. Some of the organic layers in the
multilayer structure may be omitted, or may serve more than one
function. For example, a single organic layer may serve as the
electron injection layer and the electron transport layer. Further,
the organic layers having a same function may have a laminate
structure of two or more layers, for example, the hole transport
layers may have a laminate structure of two or more layers, the
light emitting layers may have a laminate structure of two or more
layers, or the electron transport layers may have a laminate
structure of two or more layers.
[0201] Electrode materials with high work functions such as ITO and
gold are used as the anode of the organic EL device of the present
invention.
[0202] As the hole injection layer of the organic EL device of the
present invention, a material obtained by p-doping an arylamine
compound represented by the above general formula (1) with an
electron acceptor is preferably used.
[0203] As hole-injecting and transporting materials which can be
mixed with or used simultaneously with the arylamine compound
represented by the above general formula (1), materials such as
starburst-type triphenylamine derivatives and various
triphenylamine tetramers; porphyrin compounds as represented by
copper phthalocyanine; accepting heterocyclic compounds such as
hexacyano azatriphenylene and coating-type polymer materials; and
the like can be used. These materials may be formed into a thin
film by a vapor deposition method or other known methods such as a
spin coating method and an inkjet method.
[0204] As the hole transport layer of the organic EL device of the
present invention, in addition to the arylamine compounds
represented by the above general formula (1), benzidine derivatives
such as N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (TPD),
N,N'-diphenyl-N,N'-di(.alpha.-naphthyl)benzidine (NPD), and
N,N,N',N'-tetrabiphenylylbenzidine, arylamine compounds having a
structure in which two triphenylamine structures are joined within
a molecule via a single bond or a divalent group that does not
contain a heteroatom, such as
1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane (TAPC), arylamine
compounds having a structure in which four triphenylamine
structures are joined within a molecule via a single bond or a
divalent group that does not contain a heteroatom, various
triphenylamine trimers, and the like can be used. Further, as the
hole injection and transport layers, coating-type polymer materials
such as poly(3,4-ethylenedioxythiophene) (PEDOT)/poly(styrene
sulfonate) (PSS) can be used.
[0205] As the hole transport layer of the organic EL device of the
present invention, hole-transporting arylamine compounds are
preferably used, and particularly, the arylamine compounds
represented by the above general formula (1) are preferably used.
Then, the compounds which are not p-doped are preferably used.
[0206] These may be individually deposited for film forming, but
may be used as a single layer deposited mixed with other materials,
or may be formed as a laminate of individually deposited layers, a
laminate of mixedly deposited layers, or a laminate of an
individually deposited layer and a mixedly deposited layer. These
materials may be formed into a thin film by a vapor deposition
method or other known methods such as a spin coating method and an
inkjet method.
[0207] As the electron blocking layer of the organic EL device of
the present invention, the arylamine compounds represented by the
above general formula (1) are preferably used, however, in addition
thereto, arylamine compounds having a structure in which four
triphenylamine structures are joined within a molecule via a single
bond or a divalent group that does not contain a heteroatom,
arylamine compounds having a structure in which two triphenylamine
structures are joined within a molecule via a single bond or a
divalent group that does not contain a heteroatom, compounds having
an electron blocking effect, including, for example, carbazole
derivatives such as 4,4',4''-tri(N-carbazolyl)triphenylamine
(TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene,
1,3-bis(carbazol-9-yl)benzene (mCP), and
2,2-bis(4-carbazol-9-ylphenyl)adamantane (Ad-Cz), and compounds
having a triphenylsilyl group and a triarylamine structure, as
represented by
9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene
can be used. These may be individually deposited for film forming,
but may be used as a single layer deposited mixed with other
materials, or may be formed as a laminate of individually deposited
layers, a laminate of mixedly deposited layers, or a laminate of an
individually deposited layer and a mixedly deposited layer. These
materials may be formed into a thin film by using a vapor
deposition method or other known methods such as a spin coating
method and an inkjet method.
[0208] In the organic EL device of the present invention, it is
preferable that layers (for example, the hole transport layer, the
electron blocking layer, etc.) adjacent to the light emitting layer
are not p-doped with an electron acceptor.
[0209] In these layers, arylamine compounds having high electron
blocking performance are preferably used, and the arylamine
compounds represented by the above general formula (1) and the like
are preferably used.
[0210] Further, the film thickness of these layers is not
particularly limited as long as it is a commonly used film
thickness, however, as the hole transport layer, a layer having a
film thickness of 20 to 100 nm is used, and as the electron
blocking layer, a layer having a film thickness of 5 to 30 nm is
used.
[0211] Examples of material used for the light emitting layer of
the organic EL device of the present invention can be various metal
complexes, anthracene derivatives, bis(styryl)benzene derivatives,
pyrene derivatives, oxazole derivatives, and polyparaphenylene
vinylene derivatives, in addition to quinolinol derivative metal
complexes such as Alq.sub.3. Further, the light emitting layer may
be made of a host material and a dopant material. Examples of the
host material can be preferably anthracene derivatives. Other
examples of the host material can be thiazole derivatives,
benzimidazole derivatives, and polydialkyl fluorene derivatives, in
addition to the above light-emitting materials. Examples of the
dopant material can be preferably pyrene derivatives, amine
derivatives of the general formula (7) having a condensed ring.
Other examples of the dopant material can be quinacridone,
coumarin, rubrene, perylene, derivatives thereof, benzopyran
derivatives, indenophenanthrene derivatives, rhodamine derivatives,
and aminostyryl derivatives. These may be individually deposited
for film forming, may be used as a single layer deposited mixed
with other materials, or may be formed as a laminate of
individually deposited layers, a laminate of mixedly deposited
layers, or a laminate of the individually deposited layer and the
mixedly deposited layer.
[0212] Further, the light-emitting material may be a phosphorescent
material. Phosphorescent materials as metal complexes of metals
such as iridium and platinum may be used. Examples of the
phosphorescent materials include green phosphorescent materials
such as Ir(ppy).sub.3, blue phosphorescent materials such as FIrpic
and FIr6, and red phosphorescent materials such as
Btp.sub.2Ir(acac). Here, carbazole derivatives such as
4,4'-di(N-carbazolyl)biphenyl (CBP), TCTA, and mCP may be used as
the hole injecting and transporting host material. Compounds such
as p-bis(triphenylsilyl)benzene (UGH2) and
2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TPBI)
may be used as the electron transporting host material. In this
way, a high-performance organic EL device can be produced.
[0213] In order to avoid concentration quenching, the doping of the
host material with the phosphorescent light-emitting material
should preferably be made by co-evaporation in a range of 1 to 30
weight percent with respect to the whole light emitting layer.
[0214] Further, examples of the light-emitting material may be
delayed fluorescent-emitting material such as a CDCB derivative of
PIC-TRZ, CC2TA, PXZ-TRZ, 4CzIPN or the like (refer to Non-Patent
Document 3, for example).
[0215] These materials may be formed into a thin-film by using a
vapor deposition method or other known methods such as a spin
coating method and an inkjet method.
[0216] The hole blocking layer of the organic EL device of the
present invention may be formed by using hole blocking compounds
such as various rare earth complexes, triazole derivatives,
triazine derivatives, and oxadiazole derivatives, in addition to
phenanthroline derivatives such as bathocuproin (BCP), and the
metal complexes of quinolinol derivatives such as aluminum(III)
bis(2-methyl-8-quinolinate)-4-phenylphenolate (BAlq). These
materials may also serve as the material of the electron transport
layer. These may be individually deposited for film forming, may be
used as a single layer deposited mixed with other materials, or may
be formed as a laminate of individually deposited layers, a
laminate of mixedly deposited layers, or a laminate of the
individually deposited layer and the mixedly deposited layer. These
materials may be formed into a thin-film by using a vapor
deposition method or other known methods such as a spin coating
method and an inkjet method.
[0217] Material used for the electron transport layer of the
organic EL device of the present invention can be preferably the
compounds of the general formula (3) having an anthracene ring
structure, and the compounds of the general formula (4) having a
pyrimidine ring structure. Other examples of material can be metal
complexes of quinolinol derivatives such as Alq.sub.3 and BAlq,
various metal complexes, triazole derivatives, triazine
derivatives, oxadiazole derivatives, thiadiazole derivatives,
carbodiimide derivatives, quinoxaline derivatives, phenanthroline
derivatives, and silole derivatives. These may be individually
deposited for film forming, may be used as a single layer deposited
mixed with other materials, or may be formed as a laminate of
individually deposited layers, a laminate of mixedly deposited
layers, or a laminate of the individually deposited layer and the
mixedly deposited layer. These materials may be formed into a
thin-film by using a vapor deposition method or other known methods
such as a spin coating method and an inkjet method.
[0218] Examples of material used for the electron injection layer
of the organic EL device of the present invention can be alkali
metal salts such as lithium fluoride and cesium fluoride; alkaline
earth metal salts such as magnesium fluoride; and metal oxides such
as aluminum oxide. However, the electron injection layer may be
omitted in the preferred selection of the electron transport layer
and the cathode.
[0219] The cathode of the organic EL device of the present
invention may be made of an electrode material with a low work
function such as aluminum, or an alloy of an electrode material
with an even lower work function such as a magnesium-silver alloy,
a magnesium-indium alloy, or an aluminum-magnesium alloy.
[0220] The following describes an embodiment of the present
invention in more detail based on Examples. The present invention,
however, is not restricted to the following Examples.
Example 1
Synthesis of N,N-bis(biphenyl-4-yl)-N-(6-phenylbiphenyl-3-yl)amine
(Compound 1-2)
[0221] N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine (11.8
g), toluene (94 mL), phenylboronic acid (2.7 g), and an aqueous
solution obtained by previously dissolving potassium carbonate (5.9
g) in water (36 mL) were added into a nitrogen-substituted reaction
vessel and aerated with nitrogen gas under ultrasonic irradiation
for 30 minutes. Tetrakistriphenylphosphine palladium (0.74 g) was
added thereto, and the resulting mixture was heated and stirred at
72.degree. C. for 18 hours. After the mixture was cooled to a room
temperature, an organic layer was collected by liquid separation.
The organic layer was washed with water, and washed with a
saturated salt solution sequentially, and then dried over anhydrous
magnesium sulfate and concentrated to obtain a crude product.
Subsequently, the crude product was purified using column
chromatography, whereby a white powder of
N,N-bis(biphenyl-4-yl)-N-(6-phenylbiphenyl-3-yl)amine (Compound
1-2, 8.4 g, yield: 72%) was obtained.
[0222] The structure of the obtained white powder was identified by
NMR.
[0223] .sup.1H-NMR (CDCl.sub.3) detected 31 hydrogen signals, as
follows.
[0224] .delta. (ppm)=7.56-7.68 (7H), 7.45-7.52 (4H) 7.14-7.41
(20H)
##STR00295##
Example 2
Synthesis of
N,N-bis(biphenyl-4-yl)-N-{6-(naphthyl-1-yl)biphenyl-3-yl}amine
(Compound 1-3)
[0225] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 1-naphthylboronic acid, whereby a white powder of
N,N-bis(biphenyl-4-yl)-N-{6-(naphthyl-1-yl)biphenyl-3-yl}amine
(Compound 1-3, 9.2 g, yield: 61%) was obtained.
[0226] The structure of the obtained white powder was identified by
NMR.
[0227] .sup.1H-NMR (CDCl.sub.3) detected 33 hydrogen signals, as
follows.
[0228] .delta. (ppm)=7.84-7.87 (3H), 7.67-83 (6H), 7.26-7.64 (18H)
7.02-7.04 (6H)
##STR00296##
Example 3
Synthesis of
N,N-bis(biphenyl-4-yl)-N-{6-(9,9-dimethylfluoren-2-yl)biphenyl-3-yl}amine
(Compound 1-1)
[0229] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with (9,9-dimethylfluoren-2-yl)boronic acid, whereby a white powder
of
N,N-bis(biphenyl-4-yl)-N-{6-(9,9-dimethylfluoren-2-yl)biphenyl-3-yl}amine
(Compound 1-1, 9.0 g, yield: 57%) was obtained.
[0230] The structure of the obtained white powder was identified by
NMR.
[0231] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0232] .delta. (ppm)=7.56-7.64 (10H), 7.26-50 (18H), 7.02-7.16
(5H), 1.26 (6H)
##STR00297##
Example 4
Synthesis of
N,N-bis(biphenyl-4-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}amine
(Compound 1-4)
[0233] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, whereby a white powder of
N,N-bis(biphenyl-4-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}amine
(Compound 1-4, 8.6 g, yield: 64%) was obtained.
[0234] The structure of the obtained white powder was identified by
NMR.
[0235] .sup.1H-NMR (CDCl.sub.3) detected 35 hydrogen signals, as
follows.
[0236] .delta. (ppm)=7.66-7.53 (8H), 7.51-7.15 (27H)
##STR00298##
Example 5
Synthesis of N,N-bis(biphenyl-4-yl)-N-{6-(1,1';
4',1''-terphenyl-4-yl)biphenyl-3-yl}amine (Compound 1-9)
[0237] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-bromo-1,1'; 4',1''-terphenyl, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N,N-bis(biphenyl-4-yl)-N-{3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaboro-
lan-2-yl)phenyl}amine, whereby a white powder of
N,N-bis(biphenyl-4-yl)-N-{6-(1,1';
4',1''-terphenyl-4-yl)biphenyl-3-yl}amine (Compound 1-9, 4.5 g,
yield: 40%) was obtained.
[0238] The structure of the obtained white powder was identified by
NMR.
[0239] .sup.1H-NMR (THF-d.sub.8) detected 39 hydrogen signals, as
follows.
[0240] .delta. (ppm)=7.73-7.58 (15H), 7.46-7.12 (24H)
##STR00299##
Example 6
Synthesis of
N,N-bis(biphenyl-4-yl)-N-[6-{4-(naphthalen-1-yl)phenyl)}biphenyl-3-yl]ami-
ne (Compound 1-16)
[0241] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(naphthalen-1-yl)phenylboronic acid, whereby a white powder
of
N,N-bis(biphenyl-4-yl)-N-[6-{4-(naphthalen-1-yl)phenyl)}biphenyl-3-yl]ami-
ne (Compound 1-16, 11.6 g, yield: 77%) was obtained.
[0242] The structure of the obtained white powder was identified by
NMR.
[0243] .sup.1H-NMR (CDCl.sub.3) detected 37 hydrogen signals, as
follows.
[0244] .delta. (ppm)=7.95-7.84 (3H), 7.67-7.18 (34H)
##STR00300##
Example 7
Synthesis of
N,N-bis(biphenyl-4-yl)-N-[6-(9,9-dimethylfluoren-2-yl)phenyl)}biphenyl-3--
yl]amine (Compound 1-20)
[0245] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(9,9-dimethylfluoren-2-yl)phenylboronic acid, whereby a
white powder of
N,N-bis(biphenyl-4-yl)-N-[6-(9,9-dimethylfluoren-2-yl)phenyl)}biphenyl-3--
yl]amine (Compound 1-20, 13.1 g, yield: 81%) was obtained.
[0246] The structure of the obtained white powder was identified by
NMR.
[0247] .sup.1H-NMR (CDCl.sub.3) detected 43 hydrogen signals, as
follows.
[0248] .delta. (ppm)=7.78 (2H), 7.68-7.15 (35H), 1.55 (6H)
##STR00301##
Example 8
Synthesis of
N-(biphenyl-4-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}-N-(9,9-dimethylfluor-
en-2-yl)amine (Compound 1-56)
[0249] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(9,9-dimethylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)am-
ine, whereby a white powder of
N-(biphenyl-4-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}-N-(9,9-dimethylfluor-
en-2-yl)amine (Compound 1-56, 17.8 g, yield: 89%) was obtained.
[0250] The structure of the obtained white powder was identified by
NMR.
[0251] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0252] .delta. (ppm)=7.72-7.57 (7H), 7.52-7.33 (9H), 7.32-7.19
(17H), 1.45 (6H)
##STR00302##
Example 9
Synthesis of
N,N-bis(9,9-dimethylfluoren-2-yl)-N-(6-phenylbiphenyl-3-yl)-amine
(Compound 1-62)
[0253] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl) amine was replaced
with
N,N-bis(9,9-dimethylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)amine,
whereby a white powder of
N,N-bis(9,9-dimethylfluoren-2-yl)-N-(6-phenylbiphenyl-3-yl)amine
(Compound 1-62, 11.5 g, yield: 57%) was obtained.
[0254] The structure of the obtained white powder was identified by
NMR.
[0255] .sup.1H-NMR (THF-d.sub.8) detected 39 hydrogen signals, as
follows.
[0256] .delta. (ppm)=7.70-7.63 (3H), 7.44-7.02 (24H), 1.46
(12H)
##STR00303##
Example 10
Synthesis of N,N-bis(6-phenylbiphenyl-3-yl)-N-(biphenyl-4-yl)amine
(Compound 1-108)
[0257] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with N,N-bis(6-bromobiphenyl-3-yl)-N-(biphenyl-4-yl)amine, whereby
a white powder of
N,N-bis(6-phenylbiphenyl-3-yl)-N-(biphenyl-4-yl)amine (Compound
1-108, 10.2 g, yield: 73%) was obtained.
[0258] The structure of the obtained white powder was identified by
NMR.
[0259] .sup.1H-NMR (CDCl.sub.3) detected 35 hydrogen signals, as
follows.
[0260] .delta. (ppm)=7.57-7.66 (4H), 7.10-7.49 (31H)
##STR00304##
Example 11
Synthesis of N,N,N-tris(6-phenylbiphenyl-3-yl)amine (Compound
1-143)
[0261] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with N,N,N-tris(6-bromobiphenyl-3-yl)amine, whereby a white powder
of N,N,N-tris(6-phenylbiphenyl-3-yl)amine (Compound 1-143, 11.1 g,
yield: 75%) was obtained.
[0262] The structure of the obtained white powder was identified by
NMR.
[0263] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0264] .delta. (ppm)=7.35-7.42 (6H), 7.15-7.35 (33H)
##STR00305##
Example 12
Synthesis of
N-(biphenyl-4-yl)-N-(6-phenylbiphenyl-3-yl)-N-(9,9-dimethylfluoren-2-yl)a-
mine (Compound 1-50)
[0265] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(9,9-dimethylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)am-
ine, whereby a white powder of
N-(biphenyl-4-yl)-N-(6-phenylbiphenyl-3-yl)-N-(9,9-dimethylfluoren-2-yl)a-
mine (Compound 1-50, 13.6 g, yield: 76%) was obtained.
[0266] The structure of the obtained white powder was identified by
NMR.
[0267] .sup.1H-NMR (CDCl.sub.3) detected 35 hydrogen signals, as
follows.
[0268] .delta. (ppm)=7.72-7.61 (4H), 7.58 (2H), 7.50-7.09 (29H)
##STR00306##
Example 13
Synthesis of
N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-(6-phenylbip-
henyl-3-yl)amine (Compound 1-63)
[0269] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(6-bromobiphenyl-3-yl)-N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-1--
yl)phenyl}amine, whereby a light yellowish white powder of
N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-(6-phenylbip-
henyl-3-yl)amine (Compound 1-63, 12.2, g, yield: 56%) was
obtained.
[0270] The structure of the obtained light yellowish white powder
was identified by NMR.
[0271] .sup.1H-NMR (CDCl.sub.3) detected 37 hydrogen signals, as
follows.
[0272] .delta. (ppm)=8.10 (1H), 7.95 (1H), 7.88 (1H), 7.72-7.65
(2H), 7.60-7.10 (26H), 1.50 (6H)
##STR00307##
Example 14
Synthesis of
N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-{6-phenylbip-
henyl-3-yl}amine (Compound 1-64)
[0273] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(6-bromobiphenyl-3-yl)-N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-2--
yl)phenyl}amine, whereby a light yellowish white powder of
N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-(6-phenylbip-
henyl-3-yl)amine (Compound 1-64, 8.8 g, yield: 63%) was
obtained.
[0274] The structure of the obtained light yellowish white powder
was identified by NMR.
[0275] .sup.1H-NMR (CDCl.sub.3) detected 37 hydrogen signals, as
follows.
[0276] .delta. (ppm)=8.08 (1H), 7.76-7.94 (4H), 7.60-7.71 (4H),
7.13-7.54 (22H), 1.52 (6H)
##STR00308##
Example 15
Synthesis of
N-(biphenyl-4-yl)-N-(9,9-dimethylfluoren-2-yl)-N-{6-(4-naphthalen-1-yl-ph-
enyl)biphenyl-3-yl}amine (Compound 1-65)
[0277] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(naphthalen-1-yl)phenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(9,9-dimethylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)am-
ine, whereby a white powder of
N-(biphenyl-4-yl)-N-(9,9-dimethylfluoren-2-yl)-N-{6-(4-naphthalen-1-yl-ph-
enyl)biphenyl-3-yl}amine (Compound 1-143, 49.8 g, yield: 84%) was
obtained.
[0278] The structure of the obtained white powder was identified by
NMR.
[0279] .sup.1H-NMR (CDCl.sub.3) detected 41 hydrogen signals, as
follows.
[0280] .delta. (ppm)=7.92 (2H), 7.88 (1H), 7.72-7.18 (38H)
##STR00309##
Example 16
Synthesis of
N-(biphenyl-4-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-{6-(biphenyl-4-yl)biphe-
nyl-3-yl)}amine (Compound 1-147)
[0281] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)-N-{4-(naphthalen-1-yl)phenyl}a-
mine, whereby a white powder of
N-(biphenyl-4-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-{6-(biphenyl-4-yl)biphe-
nyl-3-yl)}amine (Compound 1-147, 7.5 g, yield: 48%) was
obtained.
[0282] The structure of the obtained white powder was identified by
NMR.
[0283] .sup.1H-NMR (CDCl.sub.3) detected 37 hydrogen signals, as
follows.
[0284] .delta. (ppm)=8.08 (1H), 7.95 (1H), 7.88 (1H), 7.68-7.18
(34H)
##STR00310##
Example 17
Synthesis of
N-(biphenyl-4-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-[6-{4-(naphthalen-1-yl)-
phenyl}biphenyl-3-yl]amine (Compound 1-148)
[0285] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(naphthalen-1-yl)phenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-(6-bromobiphenyl-3-yl)a-
mine, whereby a light yellowish white powder of
N-(biphenyl-4-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-[6-{4-(naphthalen-1-yl)-
phenyl}biphenyl-3-yl]amine (Compound 1-148, 8.4 g, yield: 60%) was
obtained.
[0286] The structure of the obtained light yellowish white powder
was identified by NMR.
[0287] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0288] .delta. (ppm)=8.09 (1H), 7.98-7.84 (5H), 7.69-7.20 (33H)
##STR00311##
Example 18
Synthesis of
N-(biphenyl-4-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-{6-(p-terphenyl-4-yl)bi-
phenyl-3-yl}amine (Compound 1-150)
[0289] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(p-terphenyl)boronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-(6-bromobiphenyl-3-yl)a-
mine, whereby a light yellowish white powder of
N-(biphenyl-4-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-{6-(p-terphenyl-4-yl)bi-
phenyl-3-yl}amine (Compound 1-150, 6.3 g, yield: 47%) was
obtained.
[0290] The structure of the obtained light yellowish white powder
was identified by NMR.
[0291] .sup.1H-NMR (CDCl.sub.3) detected 41 hydrogen signals, as
follows.
[0292] .delta. (ppm)=8.12 (1H), 7.98-7.83 (2H), 7.72-7.15 (38H)
##STR00312##
Example 19
Synthesis of
N,N-bis(biphenyl-4-yl)-N-[4-phenyl-3-{4-(naphthalen-1-yl)phenyl}phenyl]am-
ine (Compound 1-152)
[0293] 4-Bromobiphenyl (13.5 g),
2-{4-(naphthalen-1-yl)phenyl)}-4-aminobiphenyl (9.0 g), palladium
acetate (0.11 g), a toluene solution (50%) containing
tri-tert-butylphosphine (0.15 g), and toluene (90 mL) were added
into a nitrogen-substituted reaction vessel, and the mixture was
heated and stirred at 100.degree. C. for 24 hours. After insoluble
matter was removed by filtration, concentration was carried out to
obtain a crude product. Subsequently, the crude product was
purified using column chromatography, whereby a yellowish white
powder of
N,N-bis(biphenyl-4-yl)-N-[4-phenyl-3-{4-(naphthalen-1-yl)phenyl}phenyl]am-
ine (Compound 1-152, 5.4 g, yield: 33%) was obtained.
[0294] The structure of the obtained yellowish white powder was
identified by NMR.
[0295] .sup.1H-NMR (CDCl.sub.3) detected 37 hydrogen signals, as
follows.
[0296] .delta. (ppm)=7.94-7.76 (3H), 7.68-7.15 (34H)
##STR00313##
Example 20
Synthesis of
N,N-bis(9,9-dimethylfluoren-2-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}amine
(Compound 1-153)
[0297] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N,N-bis(9,9-dimethylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)amine,
whereby a light yellowish white powder of
N,N-bis(9,9-dimethylfluoren-2-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}amine
(Compound 1-153, 16.7 g, yield: 92%) was obtained.
[0298] The structure of the obtained light yellowish white powder
was identified by NMR.
[0299] .sup.1H-NMR (CDCl.sub.3) detected 43 hydrogen signals, as
follows.
[0300] .delta. (ppm)=7.80-7.59 (6H), 7.51-7.12 (25H), 1.51
(12H)
##STR00314##
Example 21
Synthesis of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-{6-(biphenyl-4-yl)biphenyl-3-yl}amin-
e (Compound 1-155)
[0301] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-(6-bromobiphenyl-3-yl)amine,
whereby a light yellowish white powder of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-{6-(biphenyl-4-yl)biphenyl-3-yl}amin-
e (Compound 1-155, 10.6 g, yield: 79%) was obtained.
[0302] The structure of the obtained light yellowish white powder
was identified by NMR.
[0303] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0304] .delta. (ppm)=8.08-8.14 (2H), 7.88-7.96 (4H), 7.24-7.64
(33H)
##STR00315##
Example 22
Synthesis of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-[6-{4-(naphthalen-1-yl)phenyl}biphen-
yl-3-yl]amine (Compound 1-156)
[0305] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(naphthalen-1-yl)phenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-(6-bromobiphenyl-3-yl)amine,
whereby a light yellowish white powder of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-[6-{4-(naphthalen-1-yl)phenyl}biphen-
yl-3-yl]amine (Compound 1-156, 10.6 g, yield: 79%) was
obtained.
[0306] The structure of the obtained light yellowish white powder
was identified by NMR.
[0307] .sup.1H-NMR (CDCl.sub.3) detected 41 hydrogen signals, as
follows.
[0308] .delta. (ppm)=8.14 (2H), 7.99-7.72 (6H), 7.61-7.10 (33H)
##STR00316##
Example 23
Synthesis of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-[6-{4-(naphthalen-2-yl)phenyl}biphen-
yl-3-yl]amine (Compound 1-157)
[0309] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(naphthalen-2-yl)phenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-(6-bromobiphenyl-3-yl)amine,
whereby a light yellowish white powder of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-[6-{4-(naphthalen-2-yl)phenyl}biphen-
yl-3-yl]amine (Compound 1-157, 9.7 g, yield: 74%) was obtained.
[0310] The structure of the obtained light yellowish white powder
was identified by NMR.
[0311] .sup.1H-NMR (CDCl.sub.3) detected 41 hydrogen signals, as
follows.
[0312] .delta. (ppm)=8.08-8.14 (3H), 7.66-7.97 (8H), 7.28-7.66
(30H)
##STR00317##
Example 24
Synthesis of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-{6-(p-terphenyl-4-yl)biphenyl-3-yl}a-
mine (Compound 1-158)
[0313] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(p-terphenyl)boronic acid pinacol ester, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-(6-bromobiphenyl-3-yl)amine,
whereby a light yellowish white powder of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-{6-(p-terphenyl-4-yl)biphenyl-3-yl}a-
mine (Compound 1-158, 6.2 g, yield: 63%) was obtained.
[0314] The structure of the obtained light yellowish white powder
was identified by NMR.
[0315] .sup.1H-NMR (CDCl.sub.3) detected 43 hydrogen signals, as
follows.
[0316] .delta. (ppm)=8.08-8.14 (3H), 7.89-7.95 (4H), 7.25-7.71
(36H)
##STR00318##
Example 25
Synthesis of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-{6-(biphenyl-2-yl)biphenyl-3-yl}amin-
e (Compound 1-159)
[0317] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 2-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with bis{4-(naphthalen-1-yl)phenyl}-N-(6-bromobiphenyl-3-yl)amine,
whereby a light yellowish white powder of
N,N-bis{4-(naphthalen-1-yl)phenyl}-N-{6-(biphenyl-2-yl)biphenyl-3-yl}amin-
e (Compound 1-159, 4.9 g, yield: 48%) was obtained.
[0318] The structure of the obtained light yellowish white powder
was identified by NMR.
[0319] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0320] .delta. (ppm)=8.08-8.12 (2H), 7.86-7.94 (4H), 7.00-7.57
(29H), 6.63-6.75 (4H)
##STR00319##
Example 26
Synthesis of
N-(biphenyl-4-yl)-N-{4-(9,9-dimethylfluoren-2-yl)phenyl}-N-(6-phenylbiphe-
nyl-3-yl)amine (Compound 1-160)
[0321] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-{4-(9,9-dimethylfluoren-2-yl)phenyl}-N-(6-bromobiphen-
yl-3-yl)amine, whereby a white powder of
N-(biphenyl-4-yl)-N-{4-(9,9-dimethylfluoren-2-yl)phenyl}-N-(6-phenylbiphe-
nyl-3-yl)amine (Compound 1-160, 8.3 g, yield: 48%) was
obtained.
[0322] The structure of the obtained white powder was identified by
NMR.
[0323] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0324] .delta. (ppm)=7.79 (2H), 7.69-7.52 (7H), 7.50-7.41 (3H),
7.40-7.10 (21H), 1.57 (6H)
##STR00320##
Example 27
Synthesis of
N-(biphenyl-4-yl)-N-{4-(9,9-dimethylfluoren-2-yl)phenyl}-N-{6-(biphenyl-3-
-yl)biphenyl-3-yl}amine (Compound 1-162)
[0325] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 3-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-{4-(9,9-dimethylfluoren-2-yl)phenyl}-N-(6-bromobiphen-
yl-3-yl)amine, whereby a white powder of
N-(biphenyl-4-yl)-N-{4-(9,9-dimethylfluoren-2-yl)phenyl}-N-{6-(biphenyl-3-
-yl)biphenyl-3-yl}amine (Compound 1-162, 8.7 g, yield: 49%) was
obtained.
[0326] The structure of the obtained white powder was identified by
NMR.
[0327] .sup.1H-NMR (CDCl.sub.3) detected 43 hydrogen signals, as
follows.
[0328] .delta. (ppm)=7.78 (2H), 7.65-7.46 (6H), 7.45-7.05 (29H),
1.54 (6H)
##STR00321##
Example 28
Synthesis of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-{6-(biphenyl-4-yl)biphe-
nyl-3-yl}amine (Compound 1-163)
[0329] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-(6-bromobiphenyl-3-yl)a-
mine, whereby a white powder of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-{6-(biphenyl-4-yl)biphe-
nyl-3-yl}amine (Compound 1-163, 4.9 g, yield: 44%) was
obtained.
[0330] The structure of the obtained white powder was identified by
NMR.
[0331] .sup.1H-NMR (CDCl.sub.3) detected 37 hydrogen signals, as
follows.
[0332] .delta. (ppm)=7.73 (1H), 7.61-7.70 (3H), 7.54-7.58 (1H),
7.19-7.52 (32H)
##STR00322##
Example 29
Synthesis of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-[6-{4-(naphthalen-1-yl)-
phenyl}biphenyl-3-yl]amine (Compound 1-164)
[0333] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(naphthalen-1-yl)phenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-(6-bromobiphenyl-3-yl)a-
mine, whereby a white powder of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-[6-{4-(naphthalen-1-yl)-
phenyl}biphenyl-3-yl]amine (Compound 1-164, 9.2 g, yield: 74%) was
obtained.
[0334] The structure of the obtained white powder was identified by
NMR.
[0335] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0336] .delta. (ppm)=8.10 (1H), 7.89-7.10 (38H)
##STR00323##
Example 30
<Synthesis of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-[6-{4-(naphthalen-2-yl)-
phenyl}biphenyl-3-yl]amine (Compound 1-165)>
[0337] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-naphthalen-2-ylphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-(6-bromobiphenyl-3-yl)a-
mine, whereby a white powder of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-[6-{4-(naphthalen-2-yl)-
phenyl}biphenyl-3-yl]amine (Compound 1-165, 9.8 g, yield: 70%) was
obtained.
[0338] The structure of the obtained white powder was identified by
NMR.
[0339] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0340] .delta. (ppm)=8.07 (2H), 7.99-7.85 (6H), 7.84-7.40 (15H),
7.39-7.12 (16H)
##STR00324##
Example 31
Synthesis of
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-(6-phenylbiphenyl-3-yl)a-
mine (Compound 1-166)
[0341] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)am-
ine, whereby a white powder of
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-(6-phenylbiphenyl-3-yl)a-
mine (Compound 1-166, 11.0 g, yield: 61%) was obtained.
[0342] The structure of the obtained white powder was identified by
NMR.
[0343] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0344] .delta. (ppm)=7.60-7.74 (4H), 7.14-7.52 (33H), 7.00-7.03
(2H)
##STR00325##
Example 32
Synthesis of
N-(p-terphenyl-4-yl)-N-(9,9-dimethylfluoren-2-yl)-N-(6-phenylbiphenyl-3-y-
l)amine (Compound 1-167)
[0345] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(p-terphenyl-4-yl)-N-(9,9-dimethylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl-
)amine, whereby a white powder of
N-(p-terphenyl-4-yl)-N-(9,9-dimethylfluoren-2-yl)-N-(6-phenylbiphenyl-3-y-
l)amine (Compound 1-167, 18.3 g, yield: 74%) was obtained.
[0346] The structure of the obtained white powder was identified by
NMR.
[0347] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0348] .delta. (ppm)=7.72-7.57 (6H), 7.51-7.11 (27H), 1.53 (6H)
##STR00326##
Example 33
Synthesis of
N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-{6-(biphenyl-
-4-yl)biphenyl-3-yl}amine (Compound 1-169)
[0349] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(9,9-dimethylfluoren-2-yl)-N-{(4-naphthalen-2-yl)phenyl}-N-(6-bromobiph-
enyl-3-yl)amine, whereby a white powder of
N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-{6-(biphenyl-
-4-yl)biphenyl-3-yl}amine (Compound 1-169, 10.4 g, yield: 67%) was
obtained.
[0350] The structure of the obtained white powder was identified by
NMR.
[0351] .sup.1H-NMR (CDCl.sub.3) detected 41 hydrogen signals, as
follows.
[0352] .delta. (ppm)=8.12 (1H), 7.78-7.92 (4H), 7.60-7.71 (6H),
7.21-7.54 (24H), 1.53 (6H)
##STR00327##
Example 34
Synthesis of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-{2-(biphenyl-4-yl)biphe-
nyl-4-yl}amine (Compound 1-170)
[0353] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-{2-(biphenyl-4-yl)-brom-
obenzen-4-yl}amine, whereby a white powder of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-{2-(biphenyl-4-yl)biphe-
nyl-4-yl}amine (Compound 1-170, 10.4 g, yield: 67%) was
obtained.
[0354] The structure of the obtained white powder was identified by
NMR.
[0355] .sup.1H-NMR (CDCl.sub.3) detected 37 hydrogen signals, as
follows.
[0356] .delta. (ppm)=8.08 (1H), 7.81-7.96 (3H), 7.79-7.81 (1H),
7.21-7.73 (32H)
##STR00328##
Example 35
Synthesis of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-[2-{4-(naphthalen-2-yl)-
phenyl}biphenyl-4-yl]amine (Compound 1-171)
[0357] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-[2-{4-(naphthalen-2-yl)-
phenyl}-(bromobiphenyl-4-yl)]amine, whereby a white powder of
N-(biphenyl-4-yl)-N-{4-(naphthalen-2-yl)phenyl}-N-[2-{4-(naphthalen-2-yl)-
phenyl}biphenyl-4-yl]amine (Compound 1-171, 10.0 g, yield: 81%) was
obtained.
[0358] The structure of the obtained white powder was identified by
NMR.
[0359] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0360] .delta. (ppm)=8.04-8.10 (2H), 7.78-7.96 (8H), 7.24-7.65
(29H)
##STR00329##
Example 36
Synthesis of
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-{6-(biphenyl-4-yl)biphen-
yl-3-yl}amine (Compound 1-174)
[0361] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)am-
ine, whereby a white powder of
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-{6-(biphenyl-4-yl)biphen-
yl-3-yl}amine (Compound 1-174, 6.5 g, yield: 71%) was obtained.
[0362] The structure of the obtained white powder was identified by
NMR.
[0363] .sup.1H-NMR (CDCl.sub.3) detected 43 hydrogen signals, as
follows.
[0364] .delta. (ppm)=7.61-7.77 (6H), 7.20-7.51 (34H), 7.06-7.11
(3H)
##STR00330##
Example 37
Synthesis of
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-{6-(biphenyl-3-yl)biphen-
yl-3-yl}amine (Compound 1-175)
[0365] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 3-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-(6-bromobiphenyl-3-yl)amin-
e, whereby a white powder of
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-{6-(biphenyl-3-yl)biphen-
yl-3-yl}amine (Compound 1-175, 8.0 g, yield: 87%) was obtained.
[0366] The structure of the obtained white powder was identified by
NMR.
[0367] .sup.1H-NMR (CDCl.sub.3) detected 43 hydrogen signals, as
follows.
[0368] .delta. (ppm)=7.70-7.76 (2H), 7.63-7.65 (2H), 7.18-7.54
(36H), 7.08-7.12 (3H)
##STR00331##
Example 38
Synthesis of
N,N-bis(9,9-dimethylfluoren-2-yl)-N-{6-(biphenyl-3-yl)biphenyl-3-yl}amine
(Compound 1-176)
[0369] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 3-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N,N-bis(9,9-dimethylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)amine,
whereby a white powder of
N,N-bis(9,9-dimethylfluoren-2-yl)-N-{6-(biphenyl-3-yl)biphenyl-3-yl}amine
(Compound 1-176, 17.0 g, yield: 85%) was obtained.
[0370] The structure of the obtained white powder was identified by
NMR.
[0371] .sup.1H-NMR (CDCl.sub.3) detected 43 hydrogen signals, as
follows.
[0372] .delta. (ppm)=7.30-7.62 (4H), 7.48-7.14 (27H), 1.50
(12H)
##STR00332##
Example 39
Synthesis of
N,N-bis(biphenyl-4-yl)-N-{6-(biphenyl-2-yl)-p-terphenyl-3-yl}amine
(Compound 1-179)
[0373] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 2-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with N,N-bis(biphenyl-4-yl)-N-(6-bromo-p-terphenyl-3-yl)amine,
whereby a white powder of
N,N-bis(biphenyl-4-yl)-N-{6-(biphenyl-2-yl)-p-terphenyl-3-yl}am-
ine (Compound 1-179, 9.6 g, yield: 86%) was obtained.
[0374] The structure of the obtained white powder was identified by
NMR.
[0375] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0376] .delta. (ppm)=7.54-7.66 (10H), 7.08-7.49 (25H), 6.63-6.74
(4H)
##STR00333##
Example 40
Synthesis of
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-{6-(biphenyl-2-yl)biphen-
yl-3-yl}amine (Compound 1-180)
[0377] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 2-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)am-
ine, whereby a white powder of
N-(biphenyl-4-yl)-N-(9,9-diphenylfluoren-2-yl)-N-{6-(biphenyl-2-yl)biphen-
yl-3-yl}amine (Compound 1-180, 5.2 g, yield: 57%) was obtained.
[0378] The structure of the obtained white powder was identified by
NMR.
[0379] .sup.1H-NMR (CDCl.sub.3) detected 43 hydrogen signals, as
follows.
[0380] .delta. (ppm)=7.60-7.74 (4H), 6.95-7.49 (35H), 6.68-6.71
(2H), 6.54-6.57 (2H)
##STR00334##
Example 41
Synthesis of
N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-{6-(biphenyl-
-4-yl)biphenyl-3-yl}amine (Compound 1-183)
[0381] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-(6-bromobiph-
enyl-3-yl)amine, whereby a white powder of
N-(9,9-dimethylfluoren-2-yl)-N-{4-(naphthalen-1-yl)phenyl}-N-{6-(biphenyl-
-4-yl)biphenyl-3-yl}amine (Compound 1-183, 19.9 g, yield: 89%) was
obtained.
[0382] The structure of the obtained white powder was identified by
NMR.
[0383] .sup.1H-NMR (CDCl.sub.3) detected 41 hydrogen signals, as
follows.
[0384] .delta. (ppm)=8.10 (1H), 7.93 (1H), 7.88 (1H), 7.71 (2H),
7.65-7.15 (30H), 1.53 (6H)
##STR00335##
Example 42
Synthesis of
N-(9,9-diphenylfluoren-2-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}aniline
(Compound 1-217)
[0385] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with N-(9,9-diphenylfluoren-2-yl)-N-(6-bromobiphenyl-3-yl)aniline,
whereby a white powder of
N-(9,9-diphenylfluoren-2-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}aniline
(Compound 1-217, 4.2 g, yield: 37%) was obtained.
[0386] The structure of the obtained white powder was identified by
NMR.
[0387] .sup.1H-NMR (CDCl.sub.3) detected 39 hydrogen signals, as
follows.
[0388] .delta. (ppm)=7.76-7.62 (4H), 7.44-7.03 (35H)
##STR00336##
Example 43
Synthesis of
N,N-bis{4-(naphthalen-2-yl)phenyl}-N-[6-{4-(naphthalen-1-yl)phenyl}biphen-
yl-3-yl]amine (Compound 1-185)
[0389] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-(naphthalen-1-yl)phenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N,N-bis{4-(naphthalen-2-yl)phenyl}-N-(6-bromobiphenyl-3-yl)amine,
whereby a white powder of
N,N-bis{4-(naphthalen-2-yl)phenyl}-N-[6-{4-(naphthalen-1-yl)phenyl}biphen-
yl-3-yl]amine (Compound 1-185, 6.5 g, yield: 73%) was obtained.
[0390] The structure of the obtained white powder was identified by
NMR.
[0391] .sup.1H-NMR (CDCl.sub.3) detected 41 hydrogen signals, as
follows.
[0392] .delta. (ppm)=8.11 (2H), 7.98-7.68 (18H), 7.59-7.23
(21H)
##STR00337##
Example 44
Synthesis of
N-(biphenyl-4-yl)-N-(phenanthren-9-yl)-N-(6-phenylbiphenyl-3-yl)amine
(Compound 1-187)
[0393] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(phenanthren-9-yl)-N-(6-bromobiphenyl-3-yl)amine,
whereby a white powder of
N-(biphenyl-4-yl)-N-(phenanthren-9-yl)-N-(6-phenylbiphenyl-3-yl)amine
(Compound 1-187, 3.5 g, yield: 22%) was obtained.
[0394] The structure of the obtained white powder was identified by
NMR.
[0395] .sup.1H-NMR (CDCl.sub.3) detected 31 hydrogen signals, as
follows.
[0396] .delta. (ppm)=8.81-8.70 (2H), 8.17 (1H), 7.83 (1H), 7.78
(1H), 7.74-7.72 (26H)
##STR00338##
Example 45
Synthesis of
N-(biphenyl-4-yl)-N-(phenanthren-9-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}-
amine (Compound 1-188)
[0397] The reaction was carried out under the same conditions as
those of Example 1, except that phenylboronic acid was replaced
with 4-biphenylboronic acid, and
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(phenanthren-9-yl)-N-(6-bromobiphenyl-3-yl)amine,
whereby a white powder of
N-(biphenyl-4-yl)-N-(phenanthren-9-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}-
amine (Compound 1-188, 13.0 g, yield: 77%) was obtained.
[0398] The structure of the obtained white powder was identified by
NMR.
[0399] .sup.1H-NMR (CDCl.sub.3) detected 35 hydrogen signals, as
follows.
[0400] .delta. (ppm)=8.82-8.73 (2H), 8.17 (1H), 7.85 (1H), 7.78
(1H), 7.75-7.09 (30H)
##STR00339##
Example 46
Synthesis of
N-(biphenyl-4-yl)-N-(9-phenylcarbazol-2-yl)-N-{6-(biphenyl-4-yl)biphenyl--
3-yl}amine (Compound 1-189)
[0401] The reaction was carried out under the same conditions as
those of Example 19, except that 4-bromobiphenyl was replaced with
2-bromo-9-phenylcarbazole, and
2-{4-(naphthalen-1-yl)phenyl)}-4-aminobiphenyl was replaced with
N-(biphenyl-4-yl)-N-{6-(biphenyl-4-yl)biphenyl-3-yl}amine, whereby
a white powder of
N-(biphenyl-4-yl)-N-(9-phenylcarbazol-2-yl)-N-{6-(biphenyl-4-yl)biphenyl--
3-yl}amine (Compound 1-189, 18.0 g, yield: 85%) was obtained.
[0402] The structure of the obtained white powder was identified by
NMR.
[0403] .sup.1H-NMR (CDCl.sub.3) detected 38 hydrogen signals, as
follows.
[0404] .delta. (ppm)=8.13-8.06 (2H), 7.65-7.59 (4H), 7.57-7.50
(6H), 7.49-7.10 (26H)
##STR00340##
Example 47
Synthesis of
N-(biphenyl-4-yl)-N-(9,9'-spirobi[9H-fluoren]-2-yl)-N-(6-phenylbiphenyl-3-
-yl)amine (Compound 1-190)
[0405] The reaction was carried out under the same conditions as
those of Example 1, except that
N,N-bis(biphenyl-4-yl)-N-(6-bromobiphenyl-3-yl)amine was replaced
with
N-(biphenyl-4-yl)-N-(9,9'-spirobi[9H-fluoren]-2-yl)-N-(6-bromobiphenyl-3--
yl)amine, whereby a white powder of
N-(biphenyl-4-yl)-N-(9,9'-spirobi[9H-fluoren]-2-yl)-N-(6-phenylbiphenyl-3-
-yl)amine (Compound 1-190, 6.0 g, yield: 52%) was obtained.
[0406] The structure of the obtained white powder was identified by
NMR.
[0407] .sup.1H-NMR (CDCl.sub.3) detected 37 hydrogen signals, as
follows.
[0408] .delta. (ppm)=7.85-7.72 (4H), 7.57 (2H), 7.49-7.29 (8H),
7.23-6.95 (17H), 6.88-6.82 (4H), 6.80-6.66 (2H)
##STR00341##
Example 48
[0409] The melting points and the glass transition points of the
arylamine compounds of the general formula (1) were measured using
a high-sensitive differential scanning calorimeter (DSC3100SA
produced by Bruker AXS).
TABLE-US-00001 Glass transition Melting point point Compound of
Example 2 242.degree. C. 103.degree. C. Compound of Example 3 No
melting point observed 115.degree. C. Compound of Example 4 No
melting point observed 104.degree. C. Compound of Example 5 No
melting point observed 117.degree. C. Compound of Example 6 No
melting point observed 107.degree. C. Compound of Example 7
240.degree. C. 127.degree. C. Compound of Example 8 No melting
point observed 116.degree. C. Compound of Example 9 No melting
point observed 119.degree. C. Compound of Example 10 No melting
point observed 101.degree. C. Compound of Example 11 No melting
point observed 112.degree. C. Compound of Example 12 No melting
point observed 102.degree. C. Compound of Example 13 No melting
point observed 109.degree. C. Compound of Example 14 237.degree. C.
108.degree. C. Compound of Example 15 No melting point observed
119.degree. C. Compound of Example 16 No melting point observed
109.degree. C. Compound of Example 17 No melting point observed
113.degree. C. Compound of Example 18 No melting point observed
121.degree. C. Compound of Example 19 No melting point observed
111.degree. C. Compound of Example 20 246.degree. C. 132.degree. C.
Compound of Example 21 No melting point observed 117.degree. C.
Compound of Example 22 No melting point observed 119.degree. C.
Compound of Example 23 245.degree. C. 120.degree. C. Compound of
Example 24 240.degree. C. 125.degree. C. Compound of Example 25 No
melting point observed 107.degree. C. Compound of Example 26
244.degree. C. 113.degree. C. Compound of Example 27 No melting
point observed 112.degree. C. Compound of Example 28 No melting
point observed 110.degree. C. Compound of Example 29 No melting
point observed 112.degree. C. Compound of Example 30 No melting
point observed 115.degree. C. Compound of Example 31 No melting
point observed 125.degree. C. Compound of Example 32 No melting
point observed 114.degree. C. Compound of Example 33 No melting
point observed 122.degree. C. Compound of Example 34 No melting
point observed 111.degree. C. Compound of Example 35 No melting
point observed 119.degree. C. Compound of Example 36 No melting
point observed 137.degree. C. Compound of Example 37 No melting
point observed 125.degree. C. Compound of Example 38 233.degree. C.
120.degree. C. Compound of Example 39 232.degree. C. 110.degree. C.
Compound of Example 40 No melting point observed 126.degree. C.
Compound of Example 41 No melting point observed 122.degree. C.
Compound of Example 42 No melting point observed 125.degree. C.
Compound of Example 43 No melting point observed 116.degree. C.
Compound of Example 44 No melting point observed 115.degree. C.
Compound of Example 45 No melting point observed 129.degree. C.
Compound of Example 46 No melting point observed 121.degree. C.
Compound of Example 47 No melting point observed 129.degree. C.
[0410] The arylamine compounds of the general formula (1) have
glass transition points of 100.degree. C. or higher, demonstrating
that the compounds have a stable thin-film state.
Example 49
[0411] A 100 nm-thick vapor-deposited film was fabricated on an ITO
substrate using the arylamine compounds of the general formula (1),
and a work function was measured using an ionization potential
measuring device (PYS-202 produced by Sumitomo Heavy Industries,
Ltd.).
TABLE-US-00002 Work function Compound of Example 1 5.68 eV Compound
of Example 2 5.72 eV Compound of Example 3 5.66 eV Compound of
Example 4 5.67 eV Compound of Example 5 5.70 eV Compound of Example
6 5.71 eV Compound of Example 7 5.66 eV Compound of Example 8 5.62
eV Compound of Example 9 5.55 eV Compound of Example 10 5.72 eV
Compound of Example 11 5.75 eV Compound of Example 12 5.62 eV
Compound of Example 13 5.62 eV Compound of Example 14 5.62 eV
Compound of Example 15 5.63 eV Compound of Example 16 5.73 eV
Compound of Example 17 5.69 eV Compound of Example 18 5.71 eV
Compound of Example 19 5.72 eV Compound of Example 20 5.55 eV
Compound of Example 21 5.72 eV Compound of Example 22 5.73 eV
Compound of Example 23 5.72 eV Compound of Example 24 5.73 eV
Compound of Example 25 5.73 eV Compound of Example 26 5.63 eV
Compound of Example 27 5.64 eV Compound of Example 28 5.69 eV
Compound of Example 29 5.69 eV Compound of Example 30 5.67 eV
Compound of Example 31 5.66 eV Compound of Example 32 5.61 eV
Compound of Example 33 5.62 eV Compound of Example 34 5.70 eV
Compound of Example 35 5.71 eV Compound of Example 36 5.67 eV
Compound of Example 37 5.68 eV Compound of Example 38 5.58 eV
Compound of Example 39 5.72 eV Compound of Example 40 5.64 eV
Compound of Example 41 5.63 eV Compound of Example 42 5.71 eV
Compound of Example 43 5.68 eV Compound of Example 44 5.76 eV
Compound of Example 45 5.74 eV Compound of Example 46 5.60 eV
Compound of Example 47 5.64 eV
[0412] As the results show, the arylamine compounds of the general
formula (1) have desirable energy levels compared to the work
function 5.4 eV of common hole transport materials such as NPD and
TPD, and thus possess desirable hole transportability.
Example 50
Synthesis of
N5',N5',N9',N9'-tetrakis{4-(tert-butyl)phenyl}spiro(fluorene-9,7'-fluoren-
o[4,3-b]benzofuran)-5',9'-diamine (Compound 7-1)
[0413] 5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran)
(5.0 g), bis{4-(tert-butyl)phenyl}amine (6.0 g), palladium acetate
(0.08 g), sodium tert-butoxide (3.4 g), tri-tert-butylphosphine
(0.07 g), and toluene (60 mL) were added into a
nitrogen-substituted reaction vessel and the mixture was heated and
stirred for 2 hours under reflux. The mixture was cooled to a room
temperature, dichloromethane and water were added, and an organic
layer was collected by liquid separation. After the organic layer
was concentrated, purification by column chromatography was
performed to obtain a powder of
N5',N5',N9',N9'-tetrakis{4-(tert-butyl)phenyl}spiro(fluorene-9,7'-fluoren-
o[4,3-b]benzofuran)-5',9'-diamine (Compound 7-1; 3.1 g; yield
36%)
##STR00342##
Example 51
Synthesis of
N2,N2,N7,N7-tetrakis{4-(tert-butyl)phenyl}spiro(dibenzo[5,6:7,8]fluoreno[-
4,3-b]benzofuran-5,9'-fluorene)-2,7-diamine (Compound 7-2)
[0414] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
2,7-dibromospiro(dibenzo[5,6:7,8]fluoreno[4,3-b]benzofuran-5,9'-fluo-
rene). As a result, a powder of
N2,N2,N7,N7-tetrakis{4-(tert-butyl)phenyl}spiro(dibenzo[5,6:7,8]fluoreno[-
4,3-b]benzofuran-5,9'-fluorene)-2,7-diamine (Compound 7-2; 2.5 g;
yield 31%) was obtained.
##STR00343##
Example 52
Synthesis of
N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro(benzo[5,6]fluoreno[4,3-b]-
benzofuran-7,9'-fluorene)-5,9-diamine (Compound 7-3)
[0415] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
5,9-dibromospiro(benzo[5,6]fluoreno[4,3-b]benzofuran-7,9'-fluorene).
As a result, a powder of
N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro(benzo[5,6]fluoreno[4,3-b]-
benzofuran-7,9'-fluorene)-5,9-diamine (Compound 7-3; 3.0 g; yield
36%) was obtained.
##STR00344##
Example 53
Synthesis of
N6',N6',N10',N10'-tetrakis{4-(tert-butyl)phenyl}spiro(fluorene-9,8'-fluor-
eno[3,4-b]benzofuran)-6',10'-diamine (Compound 7-4)
[0416] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
6',10'-dibromospiro(fluorene-9,8'-fluoreno[3,4-b]benzofuran). As a
result, a powder of
N6',N6',N10',N10'-tetrakis{4-(tert-butyl)phenyl}spiro(fluorene-9,8'-fluor-
eno[3,4-b]benzofuran)-6',10'-diamine (Compound 7-4; 2.5 g; yield
34%) was obtained.
##STR00345##
Example 54
Synthesis of
N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro(fluoreno[4,3-b]benzofuran-
-7,9'-xanthene)-5,9-diamine (Compound 7-5)
[0417] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
5,9-dibromospiro(fluoreno[4,3-b]benzofuran-7,9'-xanthene). As a
result, a powder of
N5,N5,N9,N9-tetrakis{4-(tert-butyl)phenyl}spiro(fluoreno[4,3-b]benzofuran-
-7,9'-xanthene)-5,9-diamine (Compound 7-5; 2.4 g; yield 28%) was
obtained.
##STR00346##
Example 55
Synthesis of
N5',N9'-bis(biphenyl-4-yl)-N5',N9'-bis{4-(tert-butyl)phenyl}-2-fluorospir-
o(fluorene-9,7'-fluoreno[4,3-b]benzofuran)-5',9'-diamine (Compound
7-6)
[0418] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
5',9'-dibromo-2-fluorospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran)-
, and bis{4-(tert-butyl)phenyl}amine was replaced with
(biphenyl-4-yl)-{4-(tert-butyl)phenyl}amine. As a result, a powder
of
N5',N9'-bis(biphenyl-4-yl)-N5',N9'-bis{4-(tert-butyl)phenyl}-2-fluorospir-
o(fluorene-9,7'-fluoreno[4,3-b]benzofuran)-5',9'-diamine (Compound
7-6; 2.4 g; yield 28%) was obtained.
##STR00347##
Example 56
Synthesis of
N5,N9-bis{4-(tert-butyl)phenyl}-N5,N9-bis{4-(trimethylsilyl)phenyl}spiro(-
benzo[5,6]fluoreno[4,3-b]benzofuran-7,9'-fluorene)-5,9-diamine
(Compound 7-7)
[0419] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
5,9-dibromospiro(benzo[5,6]fluoreno[4,3-b]benzofuran-7,9'-fluorene),
and bis{4-(tert-butyl)phenyl}amine was replaced with
{4-(tert-butyl)phenyl}-{4-(trimethylsilyl)phenyl}amine. As a
result, a powder of
N5,N9-bis{4-(tert-butyl)phenyl}-N5,N9-bis{4-(trimethylsilyl)phe-
nyl}spiro(benzo[5,6]fluoreno[4,3-b]benzofuran-7,9'-fluorene)-5,9-diamine
(Compound 7-7; 3.0 g; yield 35%) was obtained.
##STR00348##
Example 57
Synthesis of
N5',N9'-bis{4-(tert-butyl)phenyl}-N5',N9'-bis{4-(trimethylsilyl)phenyl}sp-
iro(fluorene-9,7'-fluoreno[4,3-b]benzothiophene)-5',9'-diamine
(Compound 7-8)
[0420] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzothiophene),
and bis{4-(tert-butyl)phenyl}amine was replaced with
{4-(tert-butyl)phenyl}-{4-(trimethylsilyl)phenyl}amine. As a
result, a powder of
N5',N9'-bis{4-(tert-butyl)phenyl}-N5',N9'-bis{4-(trimethylsilyl-
)phenyl}spiro(fluorene-9,7'-fluoreno[4,3-b]benzothiophene)-5',9'-diamine
(Compound 7-8; 3.2 g; yield 37%) was obtained.
##STR00349##
Example 58
Synthesis of
N5,N9-bis(biphenyl-4-yl)-N5,N9-bis{4-(tert-butyl)phenyl}spiro(benzo[4',5'-
]thieno[2',3':5,6]fluoreno[4,3-b]benzofuran-7,9'-fluorene)-5,9-diamine
(Compound 7-9)
[0421] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
5,9-dibromospiro(benzo[4',5']thieno[2',3':5,6]fluoreno[4,3-b]benzofu-
ran-7,9'-fluorene), and bis{4-(tert-butyl)phenyl}amine was replaced
with {4-(tert-butyl)phenyl}-(biphenyl-4-yl)amine. As a result, a
powder of
N5,N9-bis(biphenyl-4-yl)-N5,N9-bis{4-(tert-butyl)phenyl}spiro(benzo[4',5'-
]thieno[2',3':5,6]fluoreno[4,3-b]benzofuran-7,9'-fluorene)-5,9-diamine
(Compound 7-9; 2.8 g; yield 34%) was obtained.
##STR00350##
Example 59
Synthesis of
N5',N5',N9',N9'-tetrakis{4-(tert-butyl)phenyl}-12',12'-dimethyl-12'H-spir-
o(fluorene-9,7'-indeno[1,2-a]fluorene)-5',9'-diamine (Compound
7-10)
[0422] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
5',9'-dibromo-12',12'-dimethyl-12'H-spiro(fluorene-9,7'-indeno[1,2-a-
]fluorene). As a result, a powder of
N5',N5',N9',N9'-tetrakis{4-(tert-butyl)phenyl}-12',12'-dimethyl-12'H-spir-
o(fluorene-9,7'-indeno[1,2-a]fluorene)-5',9'-diamine (Compound
7-10; 1.8 g; yield 49%) was obtained.
##STR00351##
Example 60
Synthesis of
N6',N10'-bis(biphenyl-4-yl)-N6',N10'-bis{4-(tert-butyl)phenyl}-5'-methyl--
5'H-spiro(fluorene-9,8'-indeno[2,1-c]carbazole)-6',10'-diamine
(Compound 7-11)
[0423] The reaction was carried out under the same conditions as
those of Example 50, except that
5',9'-dibromospiro(fluorene-9,7'-fluoreno[4,3-b]benzofuran) was
replaced with
6',10'-dibromo-5'-methyl-5'H-spiro(fluorene-9,8'-indeno[2,1-c]carbaz-
ole), and bis{4-(tert-butyl)phenyl}amine was replaced with
{4-(tert-butyl)phenyl}-(biphenyl-4-yl)amine. As a result, a powder
of
N6',N10'-bis(biphenyl-4-yl)-N6',N10'-bis{4-(tert-butyl)phenyl}-5'-methyl--
5'H-spiro(fluorene-9,8'-indeno[2,1-c]carbazole)-6',10'-diamine
(Compound 7-11; 2.3 g; yield 41%) was obtained.
##STR00352##
Example 61
[0424] The organic EL device, as shown in FIG. 1, was fabricated by
vapor-depositing a hole injection layer 3, a hole transport layer
4, a light emitting layer 5, an electron transport layer 6, an
electron injection layer 7, and a cathode (aluminum electrode) 8 in
this order on a glass substrate 1 on which an ITO electrode was
formed as a transparent anode 2 beforehand.
[0425] Specifically, the glass substrate 1 having ITO (film
thickness of 150 nm) formed thereon was subjected to ultrasonic
washing in isopropyl alcohol for 20 minutes and then dried for 10
minutes on a hot plate heated to 200.degree. C. After UV ozone
treatment for 15 minutes, the glass substrate with ITO was
installed in a vacuum vapor deposition apparatus, and the pressure
was reduced to 0.001 Pa or lower. The hole injection layer 3 was
formed so as to cover the transparent anode 2 in a film thickness
of 30 nm by dual vapor deposition of the electron acceptor
(Acceptor-1) of the structural formula below and the compound (1-2)
of Example 1 at a vapor deposition rate ratio of Acceptor-1: the
compound (1-2)=3:97. The hole transport layer 4 was formed on the
hole injection layer 3 by forming the compound (1-2) of Example 1
in a film thickness of 40 nm. The light emitting layer 5 was formed
on the hole transport layer 4 in a film thickness of 20 nm by dual
vapor deposition of Compound EMD-1 of the structural formula below
and Compound EMH-1 of the structural formula below at a vapor
deposition rate ratio of EMD-1:EMH-1=5:95. The electron transport
layer 6 was formed on the light emitting layer 5 in a film
thickness of 30 nm by dual vapor deposition of the compound (3b-1)
of the structural formula below having an anthracene ring structure
and Compound ETM-1 of the structural formula below at a vapor
deposition rate ratio of the compound (3b-1): ETM-1=50:50. The
electron injection layer 7 was formed on the electron transport
layer 6 by forming lithium fluoride in a film thickness of 1 nm.
Finally, the cathode 8 was formed by vapor-depositing aluminum in a
thickness of 100 nm. The characteristics of the thus fabricated
organic EL device were measured in the atmosphere at an ordinary
temperature. Table 1 summarizes the results of emission
characteristics measurements performed by applying a DC voltage to
the fabricated organic EL device.
##STR00353## ##STR00354##
Example 62
[0426] An organic EL device was fabricated under the same
conditions as those of Example 61, except that the compound (3b-1)
having an anthracene ring structure was replaced with the compound
(4-125) having a pyrimidine ring structure as the material of the
electron transport layer 6, and the layer was formed in a film
thickness of 30 nm by dual vapor deposition of the compound (4-125)
and the compound ETM-1 of the above structural formula at a vapor
deposition rate ratio of the compound (4-125): ETM-1=50:50. The
characteristics of the organic EL device thus fabricated were
measured in the atmosphere at an ordinary temperature. Table 1
summarizes the results of measurement of emission characteristics
when applying a DC voltage to the fabricated organic EL device.
##STR00355##
Example 63
[0427] An organic EL device was fabricated under the same
conditions as those of Example 61, except that the compound (3b-1)
having an anthracene ring structure was replaced with the compound
(6-55) having a benzotriazole ring structure as the material of the
electron transport layer 6, and the layer was formed in a film
thickness of 30 nm by dual vapor deposition of the compound (6-55)
and the compound ETM-1 of the above structural formula at a vapor
deposition rate ratio of the compound (6-55): ETM-1=50:50. The
characteristics of the organic EL device thus fabricated were
measured in the atmosphere at an ordinary temperature. Table 1
summarizes the results of measurement of emission characteristics
when applying a DC voltage to the fabricated organic EL device.
##STR00356##
Example 64
[0428] An organic EL device was fabricated under the same
conditions as those of Example 61, except that the compound EMD-1
of the above structural formula was replaced with an amine
derivative (7-1) having a condensed ring structure as the material
of the light emitting layer 5, and the layer was formed in a film
thickness of 25 nm by dual vapor deposition of the amine derivative
(7-1) having a condensed ring structure and the compound EMH-1 of
the above structural formula at a vapor deposition rate ratio of
the amine derivative (7-1): EMH-1=5:95. The characteristics of the
organic EL device thus fabricated were measured in the atmosphere
at an ordinary temperature. Table 1 summarizes the results of
measurement of emission characteristics when applying a DC voltage
to the fabricated organic EL device.
##STR00357##
Example 65
[0429] An organic EL device was fabricated under the same
conditions as those of Example 62, except that the compound EMD-1
of the above structural formula was replaced with an amine
derivative (7-1) having a condensed ring structure as the material
of the light emitting layer 5, and the layer was formed in a film
thickness of 25 nm by dual vapor deposition of the amine derivative
(7-1) having a condensed ring structure and the compound EMH-1 of
the above structural formula at a vapor deposition rate ratio of
the amine derivative (7-1): EMH-1=5:95. The characteristics of the
organic EL device thus fabricated were measured in the atmosphere
at an ordinary temperature. Table 1 summarizes the results of
measurement of emission characteristics when applying a DC voltage
to the fabricated organic EL device.
Example 66
[0430] An organic EL device was fabricated under the same
conditions as those of Example 63, except that the compound EMD-1
of the above structural formula was replaced with the amine
derivative (7-1) having a condensed ring structure as the material
of the light emitting layer 5, and the layer was formed in a film
thickness of 25 nm by dual vapor deposition of the amine derivative
(7-1) having a condensed ring structure and the compound EMH-1 of
the above structural formula at a vapor deposition rate ratio of
the amine derivative (7-1): EMH-1=5:95. The characteristics of the
organic EL device thus fabricated were measured in the atmosphere
at an ordinary temperature. Table 1 summarizes the results of
measurement of emission characteristics when applying a DC voltage
to the fabricated organic EL device.
Example 67
[0431] An organic EL device was fabricated under the same
conditions as those of Example 61, except that the compound (1-2)
of Example 1 was replaced with the compound (1-4) of Example 4 as
the material of the hole injection layer 3, and the layer was
formed in a film thickness of 30 nm by dual vapor deposition of the
electron acceptor (Acceptor-1) of the above structural formula and
the compound (1-4) of Example 4 at a vapor deposition rate ratio of
Acceptor-1: the compound (1-4)=3:97, and the compound (1-2) of
Example 1 was replaced with the compound (1-4) of Example 4 as the
material of the hole transport layer 4, and the layer was formed in
a film thickness of 40 nm. The characteristics of the organic EL
device thus fabricated were measured in the atmosphere at an
ordinary temperature. Table 1 summarizes the results of measurement
of emission characteristics when applying a DC voltage to the
fabricated organic EL device.
##STR00358##
Example 68
[0432] An organic EL device was fabricated under the same
conditions as those of Example 62, except that the compound (1-2)
of Example 1 was replaced with the compound (1-4) of Example 4 as
the material of the hole injection layer 3, and the layer was
formed in a film thickness of 30 nm by dual vapor deposition of the
electron acceptor (Acceptor-1) of the above structural formula and
the compound (1-4) of Example 4 at a vapor deposition rate ratio of
Acceptor-1: the compound (1-2)=3:97, and the compound (1-2) of
Example 1 was replaced with the compound (1-4) of Example 4 as the
material of the hole transport layer 4, and the layer was formed in
a film thickness of 40 nm. The characteristics of the organic EL
device thus fabricated were measured in the atmosphere at an
ordinary temperature. Table 1 summarizes the results of measurement
of emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Example 69
[0433] An organic EL device was fabricated under the same
conditions as those of Example 63, except that the compound (1-2)
of Example 1 was replaced with the compound (1-4) of Example 4 as
the material of the hole injection layer 3, and the layer was
formed in a film thickness of 30 nm by dual vapor deposition of the
electron acceptor (Acceptor-1) of the above structural formula and
the compound (1-4) of Example 4 at a vapor deposition rate ratio of
Acceptor-1: the compound (1-2)=3:97, and the compound (1-2) of
Example 1 was replaced with the compound (1-4) of Example 4 as the
material of the hole transport layer 4, and the layer was formed in
a film thickness of 40 nm. The characteristics of the organic EL
device thus fabricated were measured in the atmosphere at an
ordinary temperature. Table 1 summarizes the results of measurement
of emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Example 70
[0434] An organic EL device was fabricated under the same
conditions as those of Example 64, except that the compound (1-2)
of Example 1 was replaced with the compound (1-4) of Example 4 as
the material of the hole injection layer 3, and the layer was
formed in a film thickness of 30 nm by dual vapor deposition of the
electron acceptor (Acceptor-1) of the above structural formula and
the compound (1-4) of Example 4 at a vapor deposition rate ratio of
Acceptor-1: the compound (1-4)=3:97, and the compound (1-2) of
Example 1 was replaced with the compound (1-4) of Example 4 as the
material of the hole transport layer 4, and the layer was formed in
a film thickness of 40 nm. The characteristics of the organic EL
device thus fabricated were measured in the atmosphere at an
ordinary temperature. Table 1 summarizes the results of measurement
of emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Example 71
[0435] An organic EL device was fabricated under the same
conditions as those of Example 65, except that the compound (1-2)
of Example 1 was replaced with the compound (1-4) of Example 4 as
the material of the hole injection layer 3, and the layer was
formed in a film thickness of 30 nm by dual vapor deposition of the
electron acceptor (Acceptor-1) of the above structural formula and
the compound (1-4) of Example 4 at a vapor deposition rate ratio of
Acceptor-1: the compound (1-4)=3:97, and the compound (1-2) of
Example 1 was replaced with the compound (1-4) of Example 4 as the
material of the hole transport layer 4, and the layer was formed in
a film thickness of 40 nm. The characteristics of the organic EL
device thus fabricated were measured in the atmosphere at an
ordinary temperature. Table 1 summarizes the results of measurement
of emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Example 72
[0436] An organic EL device was fabricated under the same
conditions as those of Example 66, except that the compound (1-2)
of Example 1 was replaced with the compound (1-4) of Example 4 as
the material of the hole injection layer 3, and the layer was
formed in a film thickness of 30 nm by dual vapor deposition of the
electron acceptor (Acceptor-1) of the above structural formula and
the compound (1-4) of Example 4 at a vapor deposition rate ratio of
Acceptor-1: the compound (1-4)=3:97, and the compound (1-2) of
Example 1 was replaced with the compound (1-4) of Example 4 as the
material of the hole transport layer 4, and the layer was formed in
a film thickness of 40 nm. The characteristics of the organic EL
device thus fabricated were measured in the atmosphere at an
ordinary temperature. Table 1 summarizes the results of measurement
of emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Comparative Example 1
[0437] For comparison, an organic EL device was fabricated under
the same conditions as those of Example 61, except that the
compound (1-2) of Example 1 was replaced with a compound HTM-1 of
the structural formula below as the material of the hole injection
layer 3, and the layer was formed in a film thickness of 30 nm by
dual vapor deposition of the electron acceptor (Acceptor-1) of the
above structural formula and the compound HTM-1 of the structural
formula below at a vapor deposition rate ratio of Acceptor-1:
HTM-1=3:97, and the compound (1-2) of Example 1 was replaced with
the compound HTM-1 of the structural formula below as the material
of the hole transport layer 4, and the layer was formed in a film
thickness of 40 nm. The characteristics of the organic EL device
thus fabricated were measured in the atmosphere at an ordinary
temperature. Table 1 summarizes the results of measurement of
emission characteristics when applying a DC voltage to the
fabricated organic EL device.
##STR00359##
Comparative Example 2
[0438] For comparison, an organic EL device was fabricated under
the same conditions as those of Example 62, except that the
compound (1-2) of Example 1 was replaced with the compound HTM-1 of
the structural formula below as the material of the hole injection
layer 3, and the layer was formed in a film thickness of 30 nm by
dual vapor deposition of the electron acceptor (Acceptor-1) of the
above structural formula and the compound HTM-1 of the above
structural formula at a vapor deposition rate ratio of Acceptor-1:
HTM-1=3:97, and the compound (1-2) of Example 1 was replaced with
the compound HTM-1 of the above structural formula as the material
of the hole transport layer 4, and the layer was formed in a film
thickness of 40 nm. The characteristics of the organic EL device
thus fabricated were measured in the atmosphere at an ordinary
temperature. Table 1 summarizes the results of measurement of
emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Comparative Example 3
[0439] For comparison, an organic EL device was fabricated under
the same conditions as those of Example 63, except that the
compound (1-2) of Example 1 was replaced with the compound HTM-1 of
the structural formula below as the material of the hole injection
layer 3, and the layer was formed in a film thickness of 30 nm by
dual vapor deposition of the electron acceptor (Acceptor-1) of the
above structural formula and the compound HTM-1 of the above
structural formula at a vapor deposition rate ratio of Acceptor-1:
HTM-1=3:97, and the compound (1-2) of Example 1 was replaced with
the compound HTM-1 of the above structural formula as the material
of the hole transport layer 4, and the layer was formed in a film
thickness of 40 nm. The characteristics of the organic EL device
thus fabricated were measured in the atmosphere at an ordinary
temperature. Table 1 summarizes the results of measurement of
emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Comparative Example 4
[0440] For comparison, an organic EL device was fabricated under
the same conditions as those of Example 64, except that the
compound (1-2) of Example 1 was replaced with the compound HTM-1 of
the structural formula below as the material of the hole injection
layer 3, and the layer was formed in a film thickness of 30 nm by
dual vapor deposition of the electron acceptor (Acceptor-1) of the
above structural formula and the compound HTM-1 of the above
structural formula at a vapor deposition rate ratio of Acceptor-1:
HTM-1=3:97, and the compound (1-2) of Example 1 was replaced with
the compound HTM-1 of the above structural formula as the material
of the hole transport layer 4, and the layer was formed in a film
thickness of 40 nm. The characteristics of the organic EL device
thus fabricated were measured in the atmosphere at an ordinary
temperature. Table 1 summarizes the results of measurement of
emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Comparative Example 5
[0441] For comparison, an organic EL device was fabricated under
the same conditions as those of Example 65, except that the
compound (1-2) of Example 1 was replaced with the compound HTM-1 of
the structural formula below as the material of the hole injection
layer 3, and the layer was formed in a film thickness of 30 nm by
dual vapor deposition of the electron acceptor (Acceptor-1) of the
above structural formula and the compound HTM-1 of the above
structural formula at a vapor deposition rate ratio of Acceptor-1:
HTM-1=3:97, and the compound (1-2) of Example 1 was replaced with
the compound HTM-1 of the above structural formula as the material
of the hole transport layer 4, and the layer was formed in a film
thickness of 40 nm. The characteristics of the organic EL device
thus fabricated were measured in the atmosphere at an ordinary
temperature. Table 1 summarizes the results of measurement of
emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Comparative Example 6
[0442] For comparison, an organic EL device was fabricated under
the same conditions as those of Example 66, except that the
compound (1-2) of Example 1 was replaced with the compound HTM-1 of
the structural formula below as the material of the hole injection
layer 3, and the layer was formed in a film thickness of 30 nm by
dual vapor deposition of the electron acceptor (Acceptor-1) of the
above structural formula and the compound HTM-1 of the above
structural formula at a vapor deposition rate ratio of Acceptor-1:
HTM-1=3:97, and the compound (1-2) of Example 1 was replaced with
the compound HTM-1 of the above structural formula as the material
of the hole transport layer 4, and the layer was formed in a film
thickness of 40 nm. The characteristics of the organic EL device
thus fabricated were measured in the atmosphere at an ordinary
temperature. Table 1 summarizes the results of measurement of
emission characteristics when applying a DC voltage to the
fabricated organic EL device.
Comparative Example 7
[0443] For comparison, an organic EL device was fabricated under
the same conditions as those of Example 62, except that the
compound (1-2) of Example 1 was replaced with the electron acceptor
(Acceptor-1) of the above structural formula and the compound (1-2)
of Example 1 as the material of the hole transport layer 4, and the
layer was formed in a film thickness of 40 nm by dual vapor
deposition of the electron acceptor (Acceptor-1) of the above
structural formula and the compound (1-2) of Example 1 at a vapor
deposition rate ratio of Acceptor-1: the compound (1-2)=3:97. The
characteristics of the organic EL device thus fabricated were
measured in the atmosphere at an ordinary temperature. Table 1
summarizes the results of measurement of emission characteristics
when applying a DC voltage to the fabricated organic EL device.
Comparative Example 8
[0444] For comparison, an organic EL device was fabricated under
the same conditions as those of Example 68, except that the
compound (1-4) of Example 4 was replaced with the electron acceptor
(Acceptor-1) of the above structural formula and the compound (1-4)
of Example 4 as the material of the hole transport layer 4, and the
layer was formed in a film thickness of 40 nm by dual vapor
deposition of the electron acceptor (Acceptor-1) of the above
structural formula and the compound (1-1) of Example 1 at a vapor
deposition rate ratio of Acceptor-1: the compound (1-4)=3:97. The
characteristics of the organic EL device thus fabricated were
measured in the atmosphere at an ordinary temperature. Table 1
summarizes the results of measurement of emission characteristics
when applying a DC voltage to the fabricated organic EL device.
[0445] Table 1 summarizes the results of measurement of a device
lifetime using the organic EL devices fabricated in Examples 61 to
72 and Comparative Examples 1 to 8. The device lifetime was
measured as a time elapsed until the emission luminance of 2,000
cd/m.sup.2 (initial luminance) at the start of emission was
attenuated to 1,900 cd/m.sup.2 (corresponding to 95% when taking
the initial luminance as 100%: Attenuation to 95%) when carrying
out constant current driving.
TABLE-US-00003 TABLE 1 Voltage Current Power Device Hole Hole Light
Electron [V] Luminance efficiency efficiency lifetime injection
transport emitting transport (@10 mA/ [cd/m.sup.2] [cd/A] [lm/W]
(Attenuation layer layer layer layer cm.sup.2) (@10 mA/cm.sup.2)
(@10 mA/cm.sup.2) (@10 mA/cm.sup.2) to 95%) Ex. 61 Compound
Compound EMD-1/ Compound 4.01 725 7.25 5.68 235 h 1-2/ 1-2 EMH-1
3b-1/ Acceptor-1 ETM-1 Ex. 62 Compound Compound EMD-1/ Compound
4.00 791 7.91 6.21 204 h 1-2/ 1-2 EMH-1 4-125/ Acceptor-1 ETM-1 E.x
63 Compound Compound EMD-1/ Compound 4.13 753 7.53 5.69 211 h 1-2/
1-2 EMH-1 6-55/ Acceptor-1 ETM-1 Ex. 64 Compound Compound Compound
Compound 4.05 774 7.74 6.13 322 h 1-2/ 1-2 7-1/ 3b-1/ Acceptor-1
EMH-1 ETM-1 Ex. 65 Compound Compound Compound Compound 4.05 826
8.26 6.42 314 h 1-2/ 1-2 7-1/.quadrature.EMH-1 4-125/ Acceptor-1
ETM-1 Ex. 66 Compound Compound Compound Compound 4.07 822 8.22 6.34
280 h 1-2/ 1-2 7-1/ 6-55/ Acceptor-1 EMH-1 ETM-1 Ex. 67 Compound
Compound EMD-1/ Compound 4.05 740 7.39 5.75 239 h 1-4/ 1-4 EMH-1
3b-1/ Acceptor-1 ETM-1 Ex. 68 Compound Compound EMD-1/ Compound
3.95 778 7.77 6.18 246 h 1-4/ 1-4 EMH-1 4-125/ Acceptor-1 ETM-1 Ex.
69 Compound Compound EMD-1/ Compound 4.10 806 8.06 6.11 203 h 1-4/
1-4 EMH-1 6-55/ Acceptor-1 ETM-1 Ex. 70 Compound Compound Compound
Compound 4.04 756 7.56 5.92 311 h 1-4/ 1-4 7-1/ 3b-1/ Acceptor-1
EMH-1 ETM-1 Ex. 71 Compound Compound Compound Compound 4.00 795
7.95 6.19 306 h 1-4/ 1-4 7-1/ 4-125/ Acceptor-1 EMH-1 ETM-1 Ex. 72
Compound Compound Compound Compound 4.10 826 8.26 6.38 275 h 1-4/
1-4 7-1/ 6-55/ Acceptor-1 EMH-1 ETM-1 Com. Ex. 1 HTM-1/ HTM-1
EMD-1/ Compound 4.00 671 6.71 5.28 72 h Acceptor-1 EMH-1 3b-1/
ETM-1 Com. Ex. 2 HTM-1/ HTM-1 EMD-1/ Compound 3.95 700 7.00 5.58 62
h Acceptor-1 EMH-1 4-125/ ETM-1 Com. Ex. 3 HTM-1/ HTM-1 EMD-1/
Compound 4.03 708 7.08 5.42 48 h Acceptor-1 EMH-1 6-55/ ETM-1 Com.
Ex. 4 HTM-1/ HTM-1 Compound Compound 3.99 705 7.05 5.36 85 h
Acceptor-1 7-1/ 3b-1/ EMH-1 ETM-1 Com. Ex. 5 HTM-1/ HTM-1 Compound
Compound 3.96 703 7.03 5.55 78 h Acceptor-1 7-1/ 4-125/ EMH-1 ETM-1
Com. Ex. 6 HTM-1/ HTM-1 Compound Compound 3.99 711 7.11 5.42 75 h
Acceptor-1 7-1/ 6-55/ EMH-1 ETM-1 Com. Ex. 7 Compound Compound
EMD-1/ Compound 4.00 60 0.60 0.50 1 h 1-2/ 1-2/ EMH-1 4-125/
Acceptor-1 Acceptor-1 ETM-1 Com. Ex. 8 Compound Compound EMD-1/
Compound 3.95 65 0.65 0.62 1 h 1-4/ 1-4/ EMH-1 4-125/ Acceptor-1
Acceptor-1 ETM-1
[0446] As shown in Table 1, the luminous efficiency when passing a
current with a current density of 10 mA/cm.sup.2 was 6.71 to 7.11
cd/A for the organic EL devices of Comparative Examples 1 to 6
including the hole transport layer undoped with an electron
acceptor, which was higher than 0.60 to 0.65 cd/A for the organic
EL devices of Comparative Examples 7 to 8 including the hole
transport layer also doped with an electron acceptor. Then, the
luminous efficiency was 7.25 to 8.26 cd/A, which was further
higher, for the organic EL devices of Examples 61 to 72 using the
arylamine compounds represented by the general formula (1) in the
hole injection layer. Further, also the power efficiency was 5.28
to 5.58 lm/W for the organic EL devices of Comparative Examples 1
to 6 including the hole transport layer undoped with an electron
acceptor, which was higher than 0.50 to 0.62 lm/W for the organic
EL devices of Comparative Examples 7 to 8 including the hole
transport layer also doped with an electron acceptor. Then, the
power efficiency was 5.68 to 6.42 lm/W, which was further higher,
for the organic EL devices of Examples 61 to 72 using the arylamine
compounds represented by the general formula (1) in the hole
injection layer. On the other hand, the device lifetime
(attenuation to 95%) was 45 to 85 hours for the organic EL devices
of Comparative Examples 1 to 6 including the hole transport layer
undoped with an electron acceptor, which was longer than 1 hour for
the organic EL devices of Comparative Examples 7 to 8 including the
hole transport layer also doped with an electron acceptor. Then, it
is found that the device lifetime was 203 to 322 hours, which was
further greatly increased, for the organic EL devices of Examples
61 to 72 using the arylamine compounds represented by the general
formula (1) in the hole injection layer.
[0447] It was found that the organic EL device of the present
invention can achieve an organic EL device having higher luminous
efficiency and a longer lifetime compared to the conventional
organic EL devices by selecting a specific arylamine compound
(having a specific structure) as a material of a hole injection
layer and p-doping the compound with an electron acceptor so that
holes can be efficiently injected and transported into a hole
transport layer from an electrode, and by further selecting a
specific arylamine compound (having a specific structure) without
p-doping as a material of the hole transport layer so as to improve
the carrier balance inside the organic EL device.
INDUSTRIAL APPLICABILITY
[0448] The organic EL device of the present invention in which a
specific arylamine compound (having a specific structure) and an
electron acceptor are combined so as to be able to refine the
carrier balance inside the organic EL device can enhance luminous
efficiency and also can improve durability of the organic EL
device, and therefore can be applied to, for example, home electric
appliances and illuminations.
DESCRIPTION OF REFERENCE NUMERAL
[0449] 1 Glass substrate [0450] 2 Transparent anode [0451] 3 Hole
injection layer [0452] 4 Hole transport layer [0453] 5 Light
emitting layer [0454] 6 Electron transport layer [0455] 7 Electron
injection layer [0456] 8 Cathode
* * * * *